Sulphonylaminocarbonyltriazolinones

ABSTRACT

Herbicidal sulphonylaminocarbonyltriazolinones of the formula ##STR1## in which R 1  represents hydrogen, hydroxyl or amino, or represents an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cycloalkyl aralkyl, aryl, alkoxy, alkenyloxy, alkylamino and dialkylamino, 
     R 2  represents hydrogen, hydroxyl, mercapto or amino, or represents an optionally substituted radical from the series comprising alkyl, cycloalkyl, cycloalkenyl, aralkyl, aryl, alkoxy, alkylamino and dialkylamino, and R 3  represents an optionally substituted radical from the series comprising alkyl, aralkyl, aryl and heteroaryl, 
     and salts thereof. Intermediates of the formula ##STR2## in which A 1  represents in each case optionally substituted alkyl , alkenyl, cycloalkyl, alkoxy or dialkylamino and 
     A 2  represents hydrogen, or represents in each case optionally substituted alkyl, cycloalkyl, aralkyl, aryl or alkoxy, 
     provided that both A 1  and A 2  do not simultaneously represent alkyl, are also new.

This application is a divisional, of application Ser. No. 08/031,426,filed on Mar. 15, 1993, now U.S. Pat. No. 5,405,970 which is a divisionof Ser. No. 07/816,365, filed on Dec. 30, 1991, now issued to U.S. Pat.No. 5,241,074, which is a division of Ser. No. 07/692,439, filed on Apr.29, 1991, now issued to U.S. Pat. No. 5,094,683, which is a division ofSer. No. 07/556,052, filed on Jul. 20, 1990, now issued to U.S. Pat. No.5,057,144, which is a continuation-in-part of Ser. No. 07/337,775, filedon Apr. 13, 1989 now abandoned.

The invention relates to new sulphonylaminocarbonyltriazolinones, toseveral processes for their preparation, and to their use as herbicides.

It is known that certain substituted aminocarbonylimidazolinones, suchas, for example, 1-isobutylaminocarbonyl-2-imidazolidinone(isocarbamide), have herbicidal properties (cf. R. Wegler, Chemie derPflanzenschutz-und Schadlingsbekampfungsmittel [Chemistry of PlantProtection Agents and Pesticides], Vol. 5, p. 219, Springer-verlag,Berlin-Heidelberg-New York, 1977). However, the action of this compoundis not satisfactory in all respects. The newsulphonylaminocarbonyl-triazolinones of the general formula ( I )##STR3## in which R¹ represents hydrogen, hydroxyl or amino, orrepresents an optionally substituted radical from the series comprisingalkyl, alkenyl, alkinyl, cycloalkyl aralkyl, alkoxy, alkenyloxy,alkyamino and dialkylamino,

R² represents hydrogen, hydroxyl, mercapto or amino, or represents anoptionally substituted radical from the series comprising alkyl,cycloalkyl, cycloalkenyl, aralkyl, aryi, alkoxy, alkylamino anddialkylamino, and

R³ represents an optionally substituted radical from the seriescomprising alkyl, aralkyl, aryl and heteroaryl,

as well as salts of compounds of the formula (I), have now been found.

The new sulphonylaminocarbonyltriazolinones of the general formula (I)are obtained when

a) triazolinones of the general formula (II) ##STR4## in which R¹ and R²have the abovementioned meanings, are reacted with sulphonyl isocyanatesof the general formula (III )

    R.sup.3 --SO.sub.2 --N═C═O                         (III)

in which

R³ has the abovementioned meaning, if appropriate in the presence of adiluent, or when

b) triazolinone derivatives of the general formula (IV) ##STR5## inwhich R¹ and R² have the abovementioned meanings and Z representshalogen, alkoxy, aralkoxy or aryloxy, are reacted with sulphonamides ofthe general formula (V)

    R.sup.3 --SO.sub.2 --NH.sub.2                              (V)

in which

R³ has the abovementioned meaning, if appropriate in the presence of anacid acceptor and if appropriate in the presence of a diluent, or when

c) triazolinones of the general formula (II) ##STR6## in which R¹ and R²have the abovementioned meanings are reacted with sulphonamidederivatives of the general formula (VI)

    R.sup.3 --SO.sub.2 --NH--CO--Z                             (VI)

in which

R³ has the abovementioned meaning and Z represents halogen, alkoxy,aralkoxy or aryloxy, if appropriate in the presence of an acid acceptorand if appropriate in the presence of a diluent, and, if appropriate,salts are formed by customary methods from the compounds of the formula(I) prepared by process (a), (b) or (c).

The new sulphonylaminocarbonyltriazolinones of the general formula (I)and their salts are distinguished by a powerful herbicidal activity.Surprisingly, the new compounds of the formula (I) show a considerablybetter herbicidal action than the known herbicide1-isobutyl-aminocarbonyl-2-imidazolidinone (isocarbamide), which has asimilar structure.

The invention preferably relates to compounds of the formula (I) inwhich

R¹ represents hydrogen, hydroxyl or amino, or represents C₁ -C₆ -alkylwhich is optionally substituted by fluorine, chlorine, bromine, cyano,C₁ -C₄ -alkoxy, C₁ -C₄ -alkylcarbonyl or C₁ -C₄ -alkoxy-carbonyl, orrepresents C₃ -C₆ -alkenyl or C₃ -C₆ -alkinyl, each of which isoptionally substituted by fluorine, chlorine and/or bromine, orrepresents C₃ -C₆ -cycloalkyl which is optionally substituted byfluorine, chlorine, bromine and/or C₁ -C₄ -alkyl, or representsphenyl-C₁ -C₃ -alkyl which is optionally substituted by fluorine,chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄-alkoxy and/or C₁ -C₄ -alkoxy-carbonyl, or represents phenyl which isoptionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁-C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy, fluorine- and/orchlorine-substituted C₁ -C₃ -alkoxy, C₁ -C₄ -alkylthio, fluorine- and/orchlorine-substituted C₁ -C₃ -alkylthio, C₁ -C₄ -alkylsulphinyl, C₁ -C₄-alkylsuphonyl and/or C₁ -C₄ -alkoxycarbonyl, or represents C₁ -C₆-alkoxy which is optionally substituted by fluorine, chlorine, cyano,phenyl, C₁ -C₄ -alkoxy or C₁ -C₄ -alkoxy-carbonyl, or represents C₃ -C₄-alkenyloxy, or represents C₁ -C₄ -alkylamino which is optionallysubstituted by fluorine, cyano, C₁ -C₄ -alkoxy or C₁ -C₄-alkoxy-carbonyl, or represents di-(C₁ -C₄ -alkyl)-amino,

R² represents hydrogen, hydroxyl, mercapto or amino, or represents C₁-C₆ -alkyl which is optionally substitute by fluorine, chlorine,bromine, cyano, C₃ -C₆ -cycloalkyl C₁ -C₄ -alkoxy or C₁ -C₄-alkoxy-carbonyl, or represents C₃ -C₆ -cycloalkyl which is optionallysubstituted by fluorine, chlorine, bromine and/or C₁ -C₄ alkyl, orrepresents cyclohexenyl, or represents phenyl-C₁ -C₃ -alkyl which isoptionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁-C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy and/or C₁ -C₄-alkoxy-carbonyl, or represents phenyl which is optionally substitutedby fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl,trifluoromethyl, C₁ -C₄ -alkoxy, fluorine- and/or chlorine-substitutedC₁ -C₃ alkoxy, C₁ -C₄ -alkylthio, fluorine- and/or chlorine-substitutedC₁ -C₃ -alkylthio, C₁ -C₄ -alkyl- sulphinyl, C₁ -C₄ -alkylsulphonyland/or C₁ -C₄ -alkoxy-carbonyl, or represents C₁ -C₆ -alkoxy which isoptionally substituted by fluorine, chlorine, cyano, C₁ -C₄ -alkoxy orC₁ -C₄ -alkoxy-carbonyl, or represents C₁ -C₄ -alkylamino or di-(C₁ -C₄-alkyl) -amino, and

R³ represents the group ##STR7## where R⁴ and R⁵ are identical ordifferent and represent hydrogen, fluorine, chlorine, bromine, iodine,nitro, C₁ -C₆ -alkyl (which is optionally substituted by fluorine,chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄-alkylamino-carbonyl, di-(C-C-alkyl) amino-carbonyl, hydroxyl, C₁ -C₄-alkoxy, formyloxy, C₁ -C₄ -alkyl-carbonyloxy, C₁ -C₄-alkoxy-carbonyloxy, C₁ -C₄ -alkylamino-carbonyloxy, C₁ -C₄ -alkylthio,C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, di-(C₁ -C₄-alkyl)-aminosulphonyl, C₃ -C₆ -cycloalkyl or phenyl), or represent C₂-C₆ -alkenyl (which is optionally substituted by fluorine, chlorine,bromine, cyano, C₁ -C₄ -alkoxy-carbonyl, carboxyl or phenyl), orrepresent C₂ -C₆ -alkinyl (which is optionally substitute by fluorine,chlorine, bromine, cyano, C₁ -C₄ -alkoxy-carbonyl, carboxyl or phenyl),or represent C₁ -C₄ -alkoxy (which is optionally substituted byfluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxy-carbonyl,C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄-alkylsulphonyl), or represent C₁ -C₄ -alkylthio (which is optionallysubstituted by fluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄-alkoxy-carbonyl, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄-alkylsulphonyl), or represent C₃ -C₆ C -alkenyl-oxy (which isoptionally substituted by fluorine, chlorine, bromine, cyano or C₁ -C₄-alkoxy-carbonyl), or represent C₂ -C₆ -alkenylthio (which is optionallysubstituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₃-alkylthio or C₁ -C₄ -alkoxycarbonyl), C₃ -C₆ -alkinyloxy, C₃ -C₆-alkinylthio, or represent the radical --S(O)_(p) --R⁶ where

p represents the numbers 1 or 2 and

R⁶ represents C₁ -C₄ -alkyl (which is optionally substituted byfluorine, chlorine, bromine, cyano or C₁ -C₄ -alkoxy-carbonyl), C₃ -C₆-alkenyl, C₃ -C₆ -alkinyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkoxy-C₁ -C₄-alkyl-amino, C₁ -C₄ -alkylamino, di-(C₁ -C₄ -alkyl)-amino or phenyl, orrepresents the radical --NHOR⁷ where

R⁷ represents C₁ -C₁₂ -alkyl (which is optionally substituted byfluorine, chlorine, cyano, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄-alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, C₁ -C₄ -alkylcarbonyl, C₁ -C₄-alkoxycarbonyl, C₁ -C₄ -alkylamino-carbonyl or di-(C₁ -C₄-alkyl)-aminocarbonyl), or represents C₃ -C₆ -alkenyl (which isoptionally substituted by fluorine, chlorine or bromine), C₃ -C₆-alkinyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₂ -alkyl,phenyl-C₁ -C₂ -alkyl (which is optionally substitute by fluorine,chlorine, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or C₁ -C₄-alkoxy-carbonyl), or represents benzohydryl, or represents phenyl(which is optionally substituted by fluorine, chlorine, nitro, cyano, C₁-C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy, C₁ -C₂ -fluoroalkoxy, C₁-C₄ -alkylthio, trifluoromethylthio or C₁ -C₄ -alkoxycarbonyl),

R⁴ and/or R⁵ furthermore represent phenyl or phenoxy, or represent C₁-C₄ -alkylcarbonylamino, C₁ -C₄ -alkoxycarbonylamino, C₁ -C₄-alkylamino-carbonylamino, di-(C₁ -C₄ -alkyl)amino-carbonylamino, orrepresent the radical --CO--R⁸ where

R⁸ represents C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -cycloalkoxy, C₃ -C₆-alkenyloxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylamino, C₁ -C₄ -alkoxyamino,C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl-amino or di-(C₁ -C₄ -alkyl)-amino (each ofwhich is optionally substituted by fluorine and/or chlorine),

R⁴ and/or R⁵ furthermore represent trimethylsilyl, thiazolinyl, C₁ -C₄-alkylsulphonyloxy, di-(C₁ -C₄ -alkyl)-aminosulphonylamino, or representthe radical --CH═N--R⁹ where

R⁹ represents C₁ -C₄ -alkyl which is optionally substituted by fluorine,chlorine, cyano, carboxyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, CC₁ -C₄-alkylsulphynyl or C₁ -C₄ -alkylsulphonyl, or represents benzyl which isoptionally substituted by fluorine or chlorine, or represents C₃ -C₆-alkenyl or C₃ -C₆ -alkinyl, each of which is optionally substituted byfluorine or chlorine, or represents phenyl which is optionallysubstituted by fluorine, chlorine, bromine, C₁ -C₄ -alkyl, C₁ -C₄-alkoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio, orrepresents C₁ -C₆ -alkoxy, C₃ -C₆ -alkenoxy, C₃ -C₆ -alkinoxy orbenzyloxy, each of which is optionally substituted by fluorine and/orchlorine, or represents amino, C₁ -C₄ -alkyl-amino, di-(C₁ -C₄-alkyl)-amino, phenylamino, C₁ -C₄ -alkyl-carbonyl-amino, C₁ -C₄-alkoxy-carbonylamino or C₁ -C₄ -alky-sulphonylamino, or representsphenylsulphonylamino which is optionally substituted by fluorine,chlorine, bromine or methyl,

furthermore

represents the radical ##STR8## where R¹⁰ represents hydrogen or C₁ -C₄-alkyl,

R¹¹ and R¹² are identical or different and represent hydrogen, fluorine,chlorine, bromine, nitro, cyano, C₁ -C₄ -alkyl (which is optionallysubstituted by fluorine and/or chlorine), C₁ -C₄ -alkoxy (which isoptionally substituted by fluorine and/or chlorine), carboxyl, C₁ -C₄-alkoxy-carbonyl, dimethylaminocarbonyl, C₁ -C₄ -alkylsuphonyl or di-(C₁-C₄ -alkyl)-aminosulphonyl;

furthermore

R³ represents the radical ##STR9## where R¹³ and R¹⁴ are identical ordifferent and represent hydrogen, fluorine, chlorine, bromine, nitro,cyano, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/orchlorine) or C₁ -C₄ -alkoxy (which is optionally substituted by fluorineand/or chlorine);

furthermore

R³ represents the radical ##STR10## where R¹⁵ and R¹⁶ are identical ordifferent and represent hydrogen, fluorine, chlorine, bromine, nitro,cyano, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/orchlorine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorineand/or chlorine), or represent C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinylor C₁ -C₄ -alkylsulphonyl (each of which is optionally substituted byfluorine and/or chlorine), or represent di-( C₁ -C₄-alkyl)-aminosulphonyl or C₁ -C₄ -alkoxy-carbonyl ordi-methylaminocarbonyl;

furthermore

R³ represents the radical ##STR11## where R¹⁷ and R¹⁸ are identical ordifferent and represent hydrogen fluorine, chlorine, bromine, C₁ -C₄-alkyl (which is optionally substituted by fluorine and/or bromine) C₁-C₄ -alkoxy (which is optionally substituted by fluorine and/orchlorine), or represent C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁-C₄ -alkylsulphonyl (each of which is optionally substituted by fluorineand/or chlorine), or represent di-(C₁ -C₄ -alkyl)-aminosulphonyl;

furthermore

R³ represents the radical ##STR12## where R¹⁹ and R²⁰ are identical ordifferent and represent hydrogen, fluorine, chlorine, bromine, cyano,nitro, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/orchlorine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorineand/or chlorine), C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄-alkylsulphonyl (which is optionally substituted by fluorine and/orchlorine), di-(C₁ -C₄ -alkyl)-amino-sulphonyl, C₁ -C₄ -alkoxy-carbonylor dimethylaminocarbonyl, and

A represents oxygen, sulphur or the group N--Z¹, where

Z¹ represents hydrogen, C₁ -C₄ -alkyl (which is optionally substitutedby fluorine, chlorine, bromine or cyano), C₃ -C₆ C-cycloalkyl, benzyl,phenyl (which is optionally substituted by fluorine, chlorine, bromineor nitro), C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkoxy-carbonyl or di-(C₁ -C₄-alkyl)-aminocarbonyl;

furthermore

R³ represents the radical ##STR13## where R²¹ and R²² are identical ordifferent and represent hydrogen, C₁ -C₄ -alkyl, halogen, C₁ -C₄-alkoxy-carbonyl, C₁ -C₄ -alkoxy or C₁ -C₄ -halogenoalkoxy,

Y¹ represents sulphur or the group N--R²³, where

R²³ represents hydrogen or C₁ -C₄ -alkyl;

furthermore

R³ represents the radical ##STR14## where R²⁴ represents hydrogen, C₁-C₄ -alkyl, benzyl, quinolinyl or phenyl,

R²⁵ represents hydrogen, halogen, cyano, nitro, C₁ -C₄ -alkyl (which isoptionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkoxy(which is optionally substituted by fluorine and/or chlorine),dioxolanyl or C₁ -C₄ -alkoxy-carbonyl, and

R²⁶ represents hydrogen, halogen or C₁ -C₄ -alkyl;

furthermore

R³ represents one of the groups listed below, ##STR15##

The invention furthermore preferably relates to the sodium, potassium,magnesium, calcium, ammonium, C₁ -C₄ -alkylammonium, di-(C₁ -C₄-alkyl)-ammonium, tri-(C₁ -C₄ -alkyl)-ammonium, C₅ --or C₆-cycloalkyl-ammonium and di-(C₁ -C₂ -alkyl)-benzyl-ammonium salts ofcompounds of the formula (I) in which R¹, R² and R³ have the meaningsmentioned above as being preferred.

In particular, the invention relates to compounds of the formula (I) inwhich

R¹ represents hydrogen, or represents C₁ -C₄ -alkyl which is optionallysubstituted by fluorine, chlorine, bromine, cyano, methoxy or ethoxy, orrepresents allyl, or represents C₃ -C₆ -cycloalkyl, or representsphenyl, or represents benzyl, or represents C₁ -C₃ -alkoxy, orrepresents C₁ -C₃ -alkylamino, or represents di-(C₁ -C₂ -alkyl)-amino,

R² represents hydrogen, or represents C₁ -C₄ -alkyl which is optionallysubstituted by fluorine and/or chlorine or by methoxy or ethoxy, orrepresents C₃ -C₆ -cycloalkyl, or represents phenyl, or represents C₁-C₃ -alkoxy, or represents C₁ -C₃ -alkylamino, or represents di-(C₁ -C₂-alkyl )-amino, and

R₃ represents the group ##STR16## where R₄ represents fluorine,chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy,trifluoromethoxy, 2-chloro-ethoxy, 2-methoxy-ethoxy, C₁ -C₃ -alkylthio,C₁ -C₃ -alkylsulphinyl, C₁ -C₃ -alkylsulphonyl, dimethylaminosulphonyl,diethylaminosulphonyl, N-methoxy-N-methylaminosulphonyl, phenyl, phenoxyor C₁ -C₃ -alkoxy-carbonyl, and

R⁵ represents hydrogen, fluorine, chlorine or bromine;

furthermore

R³ represents the radical ##STR17## , where R¹⁰ represents hydrogen,

R¹¹ represents fluorine, chlorine, bromine, methyl, methoxy,difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl,ethoxycarbonyl, methylsulphonyl or dimethylaminosulphonyl, and

R¹² represents hydrogen;

furthermore

R₃ represents the radical ##STR18## where R represents C₁ -C₄ -alkyl, orrepresents the radical ##STR19## where R represents C₁ -C₄ -alkyl.

Examples of the compounds according to the invention are listed in Table1 below --cf. also the Preparation Examples.

TABLE 1

    __________________________________________________________________________     ##STR20##                           (I)                                      Examples of the compounds of the formula (I)                                  R.sup.1    R.sup.2   R.sup.3                                                  __________________________________________________________________________     ##STR21## H                                                                                        ##STR22##                                                ##STR23## H                                                                                        ##STR24##                                               CH.sub.2CHCH.sub.2                                                                       C.sub.2 H.sub.5                                                                          ##STR25##                                               OCH.sub.3  C.sub.3 H.sub.7                                                                          ##STR26##                                               OCH.sub.2CHCH.sub.2                                                                       ##STR27##                                                                               ##STR28##                                               C.sub.2 H.sub.5                                                                          C.sub.4 H.sub.9 -n                                                                       ##STR29##                                               CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR30##                                                ##STR31## C.sub.3 H.sub.7                                                                          ##STR32##                                               CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR33##                                               C.sub.2 H.sub.5                                                                          C.sub.3 H.sub.7                                                                          ##STR34##                                               OC.sub.2 H.sub.5                                                                          ##STR35##                                                                               ##STR36##                                               OC.sub.3 H.sub.7                                                                         CH.sub.3                                                                                 ##STR37##                                               CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR38##                                               N(CH.sub.3).sub.2                                                                         ##STR39##                                                                               ##STR40##                                               NHCH.sub.3                                                                                ##STR41##                                                                               ##STR42##                                               CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR43##                                                ##STR44## OCH.sub.3                                                                                ##STR45##                                                ##STR46## OC.sub.2 H.sub.5                                                                         ##STR47##                                                ##STR48##                                                                                ##STR49##                                                                               ##STR50##                                                ##STR51## C.sub.3 H.sub.7                                                                          ##STR52##                                                ##STR53## C.sub.3 H.sub.7                                                                          ##STR54##                                               CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR55##                                               CH.sub.3   C.sub.4 H.sub.9                                                                          ##STR56##                                                ##STR57## C.sub.3 H.sub.7                                                                          ##STR58##                                               CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR59##                                               C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                          ##STR60##                                                ##STR61## C.sub.3 H.sub.7                                                                          ##STR62##                                               C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                          ##STR63##                                               CH.sub.3   C.sub.3 H.sub.7 -n                                                                       ##STR64##                                                ##STR65## C.sub.3 H.sub.7 -n                                                                       ##STR66##                                                ##STR67## CH.sub.3                                                                                 ##STR68##                                               CH.sub.3   C.sub.4 H.sub.9                                                                          ##STR69##                                               CH.sub.3                                                                                  ##STR70##                                                                               ##STR71##                                               C.sub.2 H.sub.5                                                                           ##STR72##                                                                               ##STR73##                                               C.sub.3 H.sub.7                                                                          C.sub.3 H.sub.7                                                                          ##STR74##                                               CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR75##                                               CH.sub.3                                                                                  ##STR76##                                                                               ##STR77##                                               OCH.sub.3  C.sub.2 H.sub.5                                                                          ##STR78##                                               OC.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                          ##STR79##                                               CH.sub.3   CH.sub.3                                                                                 ##STR80##                                               CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR81##                                                ##STR82##                                                                                ##STR83##                                                                               ##STR84##                                               CH.sub.3   CH.sub.3                                                                                 ##STR85##                                               CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR86##                                               OCH.sub.2CHCH.sub.2                                                                      C.sub. 2 H.sub.5                                                                         ##STR87##                                               OCH.sub.3  C.sub.2 H.sub.5                                                                          ##STR88##                                               CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR89##                                               CH.sub.3   CH.sub.2CHCH.sub.2                                                                       ##STR90##                                               CH.sub.3   CH.sub.2OCH.sub.3                                                                        ##STR91##                                               CH.sub.3   CH.sub.2OC.sub.2 H.sub.5                                                                 ##STR92##                                               C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4OCH.sub.3                                                                 ##STR93##                                               CH.sub.2CHCH.sub.2                                                                       H                                                                                        ##STR94##                                               CH.sub.2CHCH.sub.2                                                                       CH.sub.3                                                                                 ##STR95##                                               CH.sub.2CHCH.sub.2                                                                       C.sub.2 H.sub.5                                                                          ##STR96##                                               C.sub.2 H.sub.5                                                                           ##STR97##                                                                               ##STR98##                                               CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR99##                                               NHCH.sub.3 C.sub.2 H.sub.5                                                                          ##STR100##                                              NHCH.sub.3                                                                                ##STR101##                                                                              ##STR102##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR103##                                               ##STR104##                                                                              C.sub.2 H.sub.5                                                                          ##STR105##                                              C.sub.2 H.sub.5                                                                          C.sub.4 H.sub.9                                                                          ##STR106##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR107##                                               ##STR108##                                                                              C.sub.2 H.sub.5                                                                          ##STR109##                                              CH.sub.3                                                                                  ##STR110##                                                                              ##STR111##                                              C.sub.2 H.sub.5                                                                           ##STR112##                                                                              ##STR113##                                              OCH.sub.3  CH(CH.sub.3).sub.2                                                                       ##STR114##                                              OC.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                          ##STR115##                                              CH.sub.3   H                                                                                        ##STR116##                                              CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR117##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR118##                                              OCH.sub.3  C.sub.3 H.sub.7                                                                          ##STR119##                                              OCH.sub.3  H                                                                                        ##STR120##                                              CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR121##                                              CH.sub.2CHCH.sub.2                                                                       CH.sub.2OCH.sub.3                                                                        ##STR122##                                              CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR123##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR124##                                              CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR125##                                              CH.sub.3   C.sub.4 H.sub.9                                                                          ##STR126##                                              CH.sub.3   CH.sub.2 CH(CH.sub.3).sub.2                                                              ##STR127##                                              CH.sub.3   C(CH.sub.3).sub.3                                                                        ##STR128##                                              CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR129##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR130##                                              CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR131##                                              CH.sub.3   C.sub.4 H.sub.9                                                                          ##STR132##                                              CH.sub.3   CH.sub.2 CH(CH.sub.3).sub.2                                                              ##STR133##                                              CH.sub.3   C(CH.sub.3).sub.3                                                                        ##STR134##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR135##                                              CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR136##                                              CH.sub.3   C.sub.4 H.sub.9                                                                          ##STR137##                                              CH.sub.3   CH.sub.2 CH(CH.sub.3).sub.2                                                              ##STR138##                                              CH.sub.3   C(CH.sub.3).sub.3                                                                        ##STR139##                                              CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR140##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR141##                                              CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR142##                                              CH.sub.3   C.sub.4 H.sub.9                                                                          ##STR143##                                              CH.sub.3   CH.sub.2 CH(CH.sub.3).sub.2                                                              ##STR144##                                              CH.sub.3   C(CH.sub.3).sub.3                                                                        ##STR145##                                              CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR146##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR147##                                              CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR148##                                              CH.sub.3   C.sub.4 H.sub.9                                                                          ##STR149##                                              CH.sub.3   CH.sub.2 CH(CH.sub.3).sub.2                                                              ##STR150##                                              CH.sub.3   C(CH.sub.3).sub.3                                                                        ##STR151##                                              CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR152##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR153##                                              CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR154##                                              CH.sub.3   C.sub.4 H.sub.9                                                                          ##STR155##                                              CH.sub.3   CH.sub.2 CH(CH.sub.3).sub.2                                                              ##STR156##                                              CH.sub.3   C(CH.sub.3).sub.3                                                                        ##STR157##                                              C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                 ##STR158##                                              C.sub.3 H.sub.7                                                                          CH.sub.3                                                                                 ##STR159##                                              CH.sub.3   C(CH.sub.3).sub.3                                                                        ##STR160##                                              CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR161##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR162##                                              CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR163##                                              CH.sub.3   C.sub.4 H.sub.9                                                                          ##STR164##                                              CH.sub.3   CH.sub.2 CH(CH.sub.3).sub.2                                                              ##STR165##                                              CH.sub.3   C(CH.sub.3).sub.3                                                                        ##STR166##                                              CH.sub.3   CH.sub.3                                                                                 ##STR167##                                              CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR168##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR169##                                              CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR170##                                              CH.sub.3   C.sub.4 H.sub.9                                                                          ##STR171##                                              CH.sub.3   CH.sub.2 CH(CH.sub.3).sub.2                                                              ##STR172##                                              CH.sub.3   C(CH.sub.3).sub.3                                                                        ##STR173##                                              C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                 ##STR174##                                              CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR175##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR176##                                              CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR177##                                              CH.sub.3   C.sub.4 H.sub.9                                                                          ##STR178##                                              CH.sub.3   CH.sub.2 CH(CH.sub.3).sub.2                                                              ##STR179##                                              CH.sub.3   C(CH.sub.3).sub.3                                                                        ##STR180##                                              CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR181##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR182##                                              CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR183##                                              CH.sub.3   C.sub.4 H.sub.9                                                                          ##STR184##                                              CH.sub.3   CH.sub.2 CH(CH.sub.3).sub.2                                                              ##STR185##                                              CH.sub.3   C(CH.sub.3).sub.3                                                                        ##STR186##                                              C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                 ##STR187##                                              C.sub.3 H.sub.7                                                                          CH.sub.3                                                                                 ##STR188##                                              CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR189##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR190##                                              CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR191##                                              CH.sub.3   C.sub.4 H.sub.9                                                                          ##STR192##                                              CH.sub.3   CH.sub.2 CH(CH.sub.3).sub.2                                                              ##STR193##                                              CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR194##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR195##                                              CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR196##                                              CH.sub.3   C.sub.4 H.sub.9                                                                          ##STR197##                                              CH.sub.3   CH.sub.2 CH(CH.sub.3).sub.2                                                              ##STR198##                                              CH.sub.3   C(CH.sub.3).sub.3                                                                        ##STR199##                                              CH.sub.3   CH.sub.3                                                                                 ##STR200##                                              CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR201##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR202##                                              CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR203##                                              CH.sub.3   C.sub.4 H.sub.9                                                                          ##STR204##                                              CH.sub.3   CH.sub.2 CH(CH.sub.3).sub.2                                                              ##STR205##                                              CH.sub.3   CH.sub.3                                                                                 ##STR206##                                              CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR207##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR208##                                              CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR209##                                              CH.sub.3   C.sub.4 H.sub.9                                                                          ##STR210##                                              CH.sub.3   CH.sub.2 CH(CH.sub.3).sub.2                                                              ##STR211##                                              CH.sub.3   C(CH.sub.3).sub.3                                                                        ##STR212##                                              CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR213##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR214##                                              CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR215##                                              CH.sub.3   C.sub.4 H.sub.9                                                                          ##STR216##                                              CH.sub.3   CH.sub.2 CH(CH.sub.3).sub.2                                                              ##STR217##                                              CH.sub.3   C(CH.sub.3).sub.3                                                                        ##STR218##                                              CH.sub.3   CH.sub.3                                                                                 ##STR219##                                              CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR220##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR221##                                              CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR222##                                              CH.sub.3   C.sub.4 H.sub.9                                                                          ##STR223##                                              CH.sub.3   CH.sub.2 CH(CH.sub.3).sub.2                                                              ##STR224##                                              CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR225##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR226##                                              CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR227##                                              CH.sub.3   C.sub.4 H.sub.9                                                                          ##STR228##                                              CH.sub.3   CH.sub.2 CH(CH.sub.3).sub.2                                                              ##STR229##                                              CH.sub.3   C(CH.sub.3).sub.3                                                                        ##STR230##                                              CH.sub.3   C.sub.2 H.sub.5                                                                          ##STR231##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR232##                                              CH.sub.3   C.sub.3 H.sub.7                                                                          ##STR233##                                              CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR234##                                              CH.sub.3   C.sub.4 H.sub.9                                                                          ##STR235##                                              CH.sub.3   CH.sub.2 CH(CH.sub.3).sub.2                                                              ##STR236##                                              CH.sub.3   C(CH.sub.3).sub.3                                                                        ##STR237##                                              CH.sub.3   CH(CH.sub.3).sub.2                                                                       ##STR238##                                              CH.sub.3   C.sub.4 H.sub.9                                                                          ##STR239##                                              CH.sub.3   CH.sub.2 CH(CH.sub.3).sub.2                                                              ##STR240##                                              N(CH.sub.3).sub.2                                                                        N(CH.sub.3).sub.2                                                                        ##STR241##                                              __________________________________________________________________________

If, for example, 2,6-difluorophenyl isocyanate and5-ethyl-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one are used asstarting substances, the course of the reaction in process (a) accordingto the invention can be outlined by the following equation: ##STR242##

If, for example, 2-methylthio-benzenesulphonamide and2-chlorocarbonyl-4-dimethylamino-2,4-dihydro-3H-1,2,4-triazol-3-one areused as starting substances, the course of the reaction in process (b)according to the invention can be outlined by the following equation:##STR243##

If, for example, N-methoxycarbonyl-2-methoxy-benzenesul-phonamide and5-diethylamino-4-difluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one areused as starting substances, the course of the reaction in process (c)according to the invention can be outlined by the following equation:##STR244##

Formula (II) provides a general definition of the triazoliones to beused as starting substances in processes (a) and (c) according to theinvention for the preparation of compounds of the formula (I).

In formula (II), R¹ and R² preferably, or in particular, have thosemeanings which have already been mentioned above in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred, or particularly preferred, for R¹ and R₂.

Examples of the starting substances of the formula (II) are listed inTable 2 below.

                  TABLE 2                                                         ______________________________________                                         ##STR245##                  (II)                                             Examples of the starting substances of the                                    formula (II)                                                                  R.sup.1           R.sup.2                                                     ______________________________________                                        H                 H                                                           CH.sub.3          H                                                           C.sub.2 H.sub.5   H                                                           C.sub.3 H.sub.7   H                                                           CH(CH.sub.3).sub.2                                                                              H                                                           C.sub.4 H.sub.9   H                                                           CH.sub.2 CH(CH.sub.3).sub.2                                                                     H                                                           C(CH.sub.3).sub.3 H                                                           H                 CH.sub.3                                                    H                 C.sub.2 H.sub.5                                             H                 C.sub.3 H.sub.7                                             H                 CH(CH.sub.3).sub.2                                          H                 C.sub.4 H.sub.9                                             H                 CH.sub.2 CH(CH.sub.3).sub.2                                 H                 C(CH.sub.3).sub.3                                           CHF.sub.2         H                                                           CH.sub.2 CH.sub.2 CN                                                                            H                                                           CH.sub.2 CH.sub.2 OCH.sub.3                                                                     H                                                           H                 CF.sub.3                                                    H                 CH.sub.2 OCH.sub.3                                          H                 CH.sub.2 OC.sub.2 H.sub.5                                   H                 CH.sub.2 CH.sub.2 OCH.sub.3                                 CH.sub.3          CH.sub.3                                                    CH.sub.3          C.sub.2 H.sub.5                                             CH.sub.3          C.sub.3 H.sub.7                                             CH.sub.3          CH(CH.sub.3).sub.2                                          CH.sub.3          C.sub.4 H.sub.9                                             CH.sub.3          CH.sub.2 CH(CH.sub.3).sub.2                                 CH.sub.3          C(CH.sub.3).sub.3                                           C.sub.2 H.sub.5   CH.sub.3                                                    C.sub.3 H.sub.7   CH.sub.3                                                    CH(CH.sub.3).sub.2                                                                              CH.sub.3                                                    C.sub.4 H.sub.9   CH.sub.3                                                    CH.sub.2 CH(CH.sub.3).sub.2                                                                     CH.sub.3                                                    C.sub.2 H.sub.5   C.sub.2 H.sub.5                                             C.sub.3 H.sub.7   C.sub.3 H.sub.7                                             CHF.sub.2         C.sub.3 H.sub.7                                             CHF.sub.2         CH.sub.3                                                    CHF.sub.2         C.sub.2 H.sub.5                                             CH.sub.3          CF.sub.3                                                    C.sub.2 H.sub.5   CF.sub.3                                                    CF.sub.2 CHF.sub.2                                                                              CH.sub.3                                                    C.sub.2 H.sub.5   C.sub.3 H.sub.7                                             C.sub.2 H.sub.5   C.sub.4 H.sub.9                                             C.sub.6 H.sub.5   CH.sub.3                                                     ##STR246##       CH.sub.3                                                    CH.sub.3                                                                                         ##STR247##                                                  ##STR248##       CH.sub.3                                                     ##STR249##       CH.sub.3                                                    CH.sub.3          N(CH.sub.3).sub.2                                           C.sub.2 H.sub.5   N(CH.sub.3).sub.2                                           C.sub.2 H.sub.5                                                                                  ##STR250##                                                 C.sub.3 H.sub.7                                                                                  ##STR251##                                                 OCH.sub.3                                                                                        ##STR252##                                                  ##STR253##       C.sub.2 H.sub.5                                              ##STR254##       C.sub.3 H.sub.7                                              ##STR255##       CH.sub.3                                                     ##STR256##       C.sub.2 H.sub.5                                              ##STR257##       C.sub.3 H.sub.7                                              ##STR258##       C.sub.3 H.sub.7                                             CH.sub.3                                                                                         ##STR259##                                                 CH.sub.3                                                                                         ##STR260##                                                 NH.sub.2          CH.sub.3                                                    CH.sub.3          NHCH.sub.3                                                  NHCH.sub.3        CH.sub.3                                                    NHCH.sub.3        C.sub.2 H.sub.5                                             NHCH.sub.3        C.sub.3 H.sub.7                                             N(CH.sub.3).sub.2 CH.sub.3                                                    N(CH.sub.3).sub.2 C.sub.2 H.sub.5                                             N(CH.sub.3).sub.2 C.sub.3 H.sub.7                                             OCH.sub.3         CH.sub.3                                                    OCH.sub.3         C.sub.2 H.sub.5                                             OC.sub.2 H.sub.5  CH.sub.3                                                    OC.sub.2 H.sub.5  C.sub.2 H.sub.5                                              ##STR261##                                                                                      ##STR262##                                                  ##STR263##       CH.sub.2OC.sub.2 H.sub.5                                     ##STR264##       N(CH.sub.3).sub.2                                           OC.sub.3 H.sub.7  C.sub.3 H.sub.7                                              ##STR265##                                                                                      ##STR266##                                                  ##STR267##                                                                                      ##STR268##                                                 OCH.sub.2CHCH.sub.2                                                                             CH.sub.3                                                    OCH.sub.2CHCH.sub.2                                                                             C.sub.2 H.sub.5                                             OCH.sub.2CHCH.sub.2                                                                             C.sub.3 H.sub.7                                              ##STR269##       C.sub.3 H.sub.7                                             OCH.sub.3                                                                                        ##STR270##                                                 OCH.sub.3                                                                                        ##STR271##                                                 OCH.sub.3                                                                                        ##STR272##                                                 OCH.sub.3                                                                                        ##STR273##                                                 OCH.sub.3                                                                                        ##STR274##                                                 OCH.sub.3         N(CH.sub.3).sub.2                                           OCH.sub.2COOCH.sub.3                                                                            C.sub.3 H.sub.7                                             N(CH.sub.3).sub.2                                                                                ##STR275##                                                 N(CH.sub.3).sub.2                                                                                ##STR276##                                                 N(CH.sub.3).sub.2                                                                                ##STR277##                                                 OC.sub.2 H.sub.5  C.sub.3 H.sub.7                                             OC.sub.2 H.sub.5                                                                                 ##STR278##                                                  ##STR279##                                                                                      ##STR280##                                                  ##STR281##                                                                                      ##STR282##                                                  ##STR283##       C.sub.2 H.sub.5                                             NHCH.sub.3        CH.sub.2OCH.sub.3                                            ##STR284##       CH.sub.2OCH.sub.3                                           CH.sub.3          CH.sub.2OCH.sub.3                                           ______________________________________                                    

The starting substances of the formula (II) are known and/or can beprepared by processes known per se (cf. Chem. Ber. 90 (1957), 909-921;loc.cit. 98 (1965), 3025-3099; J. Heterocycl. Chem. 15 (1978), 237--240; Tetrahedron 32 (1976), 2347-2352; Helv. Chim. Acta 63 (1980),841-859; J. Chem. Soc. C 1967, 746-751; EP-A 283,876; EP-A 294,666; EP-A301,946; EP-A 298,371; DE-P 3,839,206/LeA 26,538 dated 19 Nov. 1988;DE-P 3,916,207/LeA 26,849 dated 18 May 1989; DE-P 3,916,208/LeA 26,850dated 18 May 1989; J. Chem. Soc. C 1970, 26-34 ; DE-P 3,916,930/LeA26,886 dated 24 May 1989).

For example, the triazolinones of the formula ( II ) are obtained when

α) oxadiazolinones of the general formula (VII) ##STR285## in which R²has the abovementioned meaning are reacted with amino compounds of thegeneral formula (VIII)

    H.sub.2 N--R.sup.1                                         (VII)

in which

R¹ has the abovementioned meaning, at temperatures between 20° C. and120° C. and, if appropriate, in the presence of a diluent, such as, forexample, water, and the hydrazine derivatives formed by this process, ofthe general formula (IX) ##STR286## in which R¹ and R² have theabovementioned meanings, are isolated by customary methods (cf. thePreparation Examples) and--or if appropriate even without intermediateisolation --the compounds of the formula (IX) are condensed attemperatures between 20° C. and 120° C. and, if appropriate, in thepresence of a basic condensation auxiliary, such as, for example, sodiumhydroxide, and, if appropriate, in the presence of a diluent, such as,for example, water, to give the compounds of the formula (II) (cf. EP-A301,946, DE-OS (German Published Specification) 3,743,493/LeA 25,759 andthe Preparation Examples),

or when

α amino compounds of the general formula (VIII)

    H.sub.2 N--R.sup.1                                         (VIII)

in which

R¹ has the abovementioned meaning, are reacted with carbonic acidderivatives, such as, for example, diphenyl carbonate, then withhydrazine or hydrazine hydrate and eventually with a carboxylic acidderivative or carbonic acid derivative of the general formula (X)

    (RO).sub.3 C--R.sup.2                                      (X)

in which

R² has the abovementioned meaning and R represents lower alkyl, attemperatures between 0° C. and 150° C. and, if appropriate, in thepresence of a diluent, such as, for example, ethylene chloride (cf. DE-P3,920,270/LeA 26,937 dated 21 Jun. 1989, DE-P 3,928,662/LeA 27,137 dated30 Aug. 1989, and the Preparation Examples).

The triazolinones of the general formula (IIa) ##STR287## in which A¹represents in each case optionally substituted alkyl, alkenyl,cycloalkyl, alkoxy or dialkylamino and

A² represents hydrogen, or represents in each case optionallysubstituted alkyl, cycloalkyl, aralkyl, aryl or alkoxy, provided thatboth A¹ and A² not simultaneously represent alkyl, are new and a subjectof the present invention.

The new triazolinones of the formula (IIa) are obtained either whenoxadiazolinones of the general formula (VlIa) ##STR288## in which A² hasthe abovementioned meaning, are reacted with amino compounds of thegeneral formula (VIIIa).

    H.sub.2 N--A.sup.1                                         (VIIIa)

in which

A¹ has the abovementioned meaning, analogously to the process describedabove under (α), or when

amino compounds of the general formula (VIIIa)

    H.sub.2 N--A.sup.1                                         (VIIIa)

are reacted with carbonic acid derivatives, then with hydrazine orhydrazine hydrate and eventually with a carboxylic acid derivative orcarbonic acid derivative of the general formula (Xa)

    (RO).sub.3 C--A.sub.2                                      (Xa)

in which

A² and R have the abovementioned meanings, analogously to the processdescribed above under (β) (also see the Preparation Examples).

In the general formula (IIa),

A¹ preferably represents C₁ -C₆ -alkyl, C₃ -C₅ -alkenyl or C₃ -C₆-cycloalkyl, or represents C₁ -C₆ -alkoxy which is optionallysubstituted by fluorine, chlorine, bromine, cyano, C₁ -C₄ -alkoxy or C₁-C₄ -alk-carbonyl, in particular methyl, ethyl, allyl, cyclopropy,methoxy, ethoxy, propoxy or isopropoxy, or represents di-(C₁ -C₄-alkyl)-amino, in particular dimethylamino or diethylamino, and

A² preferably represents hydrogen, or represents C₁ -C₈ -alkyl which isoptionally substituted by fluorine, chlorine, bromine, cyano, C₁ -C₄-alkoxy, C₁ -C₄ -alkylcarbonyl or C₁ -C₄ -alkoxy-carbonyl, or representsC₃ -C₆ -cycloalkyl which is optionally substituted by fluorine,chlorine, bromine and/or C₁ -C₄ -alkyl, or represents phenyl-C₁ -C₃-alkyl which is optionally substituted by fluorine, chlorine, bromine,cyano, nitro, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy and/or C₁-C₄ -alkoxycarbonyl, or represents phenyl which is optionallysubstituted by fluorine, chlorine bromine, cyano, nitro, C₁ -C₄ -alkyl,trifluoromethyl, C₁ -C₄ -alkoxy, fluorine- and/or chlorine-substitutedC₁ -C₃ -alkoxy, C₁ -C₄ -alkylthio, fluorine-and/or chlorine-substitutedC₁ -C₃ -alkylthio, C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl and/orC₁ -C₄ -alkoxy-carbonyl, or represents C₁ -C₄ -alkoxy, in particularhydrogen, C₁ -C₄ -alkyl which is optionally substituted by fluorineand/or chlorine, methoxy or ethoxy, or represents C₃ -C₆ -cycloalkyl, orrepresents methoxy or ethoxy,

provided that both A¹ and A² do not simultaneously represent C₁ -C₆-alkyl.

The compounds of the formulae (VII), (VIIa), (VIII), (VIlla) and (X) or(Xa) which are to used as starting substances for the preparation of thetriazolinones of the formulae (II) or (IIa) are known (cf. Helv. Chim.Acta 55 (1972), 1174 ; EP-A 301,946 ; DE-OS (German PublishedSpecification) 33,743,493).

Formula (III) provides a general definition of the sulphonyl isocyanatesfurther to be used as starting substances in process (a) according tothe invention for the preparation of compounds of the formula (I).

In formula (III), R³ preferably, or in particular, has the meaning whichhas already been mentioned above in connection with the description ofthe compounds of the formula (I) according to the invention as beingprefered or particularly preferred, for R³.

Examples of the starting substances of the formula (III) which may bementioned are:

2-fluoro-, 2-chloro-, 2-bromo-, 2-methyl-, 2-methoxy-,2-trifluoromethyl-, 2-difluoro-methoxy-, 2-trifluoromethoxy-,2-methylthio-, 2-ethylthio-, 2-propylthio-, 2-methylsuhinyl-,2-methylsulphonyl-, 2-dimethylamino-sulphonyl-,2-diethylaminosulphonyl-, 2-(N-methoxy-N-methyl)-aminosulphonyl-,2-phenyl-, 2-phenoxy-, 2-methoxycarbonyl-, 2-ethoxycarbonyl-,2-propoxycarbonyl- and 2-isopropoxycarbonyl-phenylsulphonyl isocyanate,2-fluoro-, 2-chloro-, 2-difluoromethoxy-,2-trifluorometh-2-methoxycarbonyl- and 2-ethoxycarbonyl-benzylsulphonylisocyanate, 2-methoxycarbonyl-3-thienyl-sulphonyl isocyanate4-methoxycarbonyl- and 4-ethoxycarbony-1-methyl-pyrazol-5-yl-sulphonylisocyanate.

The sulphonyl isocyanates of the formula (III) are known and/or can beprepared by processes known per se (cf. US-P 4,127,405, 4,169,719,4,371,391; EP-A 7,687, 13,480, 21,641, 23,141, 23,422, 30,139, 35,893,44,808, 44,809, 48,143, 51,466, 64,322, 70,041, 173,312).

Process (a) according to the invention for the preparation of the newcompounds of the formula (I) is preferably carried out using diluents.Suitable diluents in this context are virtually all inert organicsolvents. These preferably include aliphatic and aromatic, optionallyhalogenated hydrocarbons, such as pentane, hexane, heptane, cyclohexane,petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylenechloride, ethylene chloride, chloroform, carbon tetrachloride,chlorobenzene and o-dichlorobenzene, ethers, such as diethyl ether anddibutyl ether, glycol dimethyl ether and diglycol dimethyl ether,tetrahydrofuran and dioxane, ketones, such as acetone, methyl ethylketone, methyl isopropyl ketone and methyl isobutyl ketone, esters, suchas methyl acetate and ethyl acetate, nitriles, such as, for example,acetonitrile and propionitrile, amides, such as, for example,dimethylformamide, dimethylacetamide and N-methy-pyrroidone, and alsodimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphorictriamide.

In process (a) according to the invention, the reaction temperatures canbe varied within a substantial range. In general, the process is carriedout at temperatures between 0° C. and 150° C., preferably attemperatures between 10° C. and 80° C.

Process (a) according to the invention is generally carried out underatmospheric pressure.

For carrying out process (a) according to the invention, between 1 and 3moles, preferably between 1 and 2 moles, of sulphonyl isocyanate of theformula (III) are generally employed per mole of triazolinone of theformula (II).

The reactants can be combined in any desired sequence. The reactionmixture is stirred until the reaction is complete and concentrated, andthe crude product which remains in the residue is crystallized using asuitable solvent, such as, for example, diethyl ether. The product ofthe formula (I) which has been obtained in crystalline form is isolatedby filtration with suction.

Formula (IV) provides a general definition of the triazolinonederivatives to be used as starting substances in process (b) accordingto the invention for the preparation of compounds of the formula (I).

In formula (IV), R¹ and R², preferably, or in particular, have thosemeanings which have already been mentioned above in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred, or particularly preferred, for R¹ and R²,and

Z preferably represents chlorine, C₁ -C₄ -alkoxy, benzyloxy or phenoxy,in particular methoxy or phenoxy.

Examples of the starting substances of the formula (IV) which arepossible are the compounds of the formula (IV) to be prepared from thecompounds of the formula (II) listed in Table 2 and phosgene, methylchloroformate, benzyl chloroformate, phenyl chloroformate or diphenylcarbonate.

The starting substances of the formula (IV) are known and/or can beprepared by processes known per se (cf. EP-A 283,876 ; EP-A 294,666 ;EP-A 298,371.

The triazolinone derivatives of the formula (IV) are obtained forexample when triazolinones of the general formula (II) ##STR289## inwhich R¹ and R² have the abovementioned meanings, are reacted withcarbonic acid derivatives of the general formula (XI)

    Z--CO--Z.sup.1                                             (XI)

in which

Z has the abovementioned meaning and

Z¹ represents a leaving group, such as chlorine, methoxy, benzyloxy orphenoxy, at temperatures between -20° C. and +100° C., if appropriate inthe presence of a diluent, such as, for example, tetrahydrofuran, and,if appropriate, in the presence of an acid acceptor, such as, forexample, sodium hydride or potassium tert-butylate (cf. the PreparationExamples).

Formula (V) provides a general definition of the sulphonanides furtherto be used as starting substances in process (b) according to theinvention for the prepar-ation of compounds of the formula (I).

In formula (V), R³ preferably, or in particular, has the meaning whichhas already been mentioned above in connection with the description ofthe compounds of the formula (I) according to the invention as beingpreferred, or particularly preferred, for R³.

Examples of the starting substances of the formula (V) which may bementioned are:

2-fluoro-, 2-chloro-, 2-bromo-, 2-methyl-, 2-methoxy-,2-trifluoromethyl-, 2-difluoro-methoxy-, 2-trifluoromethoxy-,2-methylthio-, 2-ethylthio-, 2-propylthio-, 2-methylsulphinyl-,2-methylsulphonyl-, 2-dimethylaminosulphonyl-, 2-diethylaminosulphonyl-,2-(N-methoxy-N-methyl)-aminosulphonyl-, 2-phenyl-, 2-phenoxy-,2-methoxycarbonyl-, 2-ethoxycarbonyl-, 2-propoxycarbonyl- and2-isopropoxycarbonyl-benzenesulphonamide, 2-fluoro-, 2-chloro-,2-difluoromethoxy-, 2-trifluoromethoxy-, 2-methoxycarbonyl- and2-ethoxycarbonyl-phenylmethanesul-phonamide,2-methoxycarbonyl-3-thiophenesulphonamide, 4-methoxycarbonyl- and4-ethoxycarbonyl-1-methyl-pyrazol-5-sulphonamide.

The sulphonamides of the formula (V) are known and/or can be prepared byprocesses known per se (cf. US-P 4,127,405, 4,169,719, 4,371,391 ; EP-A7,687, 13,480, 21,641, 23,141, 23,422, 30,422, 30,139, 35,893, 44,808,4,809, 48,143, 51,466, 64,322, 70,041, 173,312).

Process (b) according to the invention for the preparation of the newcompounds of the formula (I) is preferably carried out using diluents.Suitable diluents in this context are virtually all inert organicsolvents, for example those which have been indicated above in the caseof process (a) according to the invention.

Acid acceptors which can be employed in process (b) according to theinvention are all acid-bind-ing agents which can customarily be used forreactions of this type. The following are preferably suitable: alkalimetal hydroxides, such as, for example, sodium hydroxide and potassiumhydroxide, alkaline earth metal hydroxides, such as, for example,calcium hydroxide, alkali metal carbonates and alkali metal alcoholares,such as sodium carbonate, potassium carbonate, sodium tert-butylate andpotassium tert-butylate, furthermore aliphatic, aromatic or heterocyclicamines, for example triethylamine, trimethylamine, dimethylaniline,dimethylbenzylamine, pyridine, 1,5-diazabicyclo-[4,3,0]-non-5-ene (DBN),1,8-diazabicyclo-[5,4,0]-undec-7-ene (DBU) and1,4-diazabicyclo-[2,2,2]-octane (DABCO).

When carrying out process (b) according to the invention, the reactiontemperatures can be varied within a substantial range. In general, theprocess is carried out at temperatures between 0° C. and 100° C.,preferably at temperatures between 10° C. and 60° C.

In general, process (b) according to the invention is carried out underatmospheric pressure. However, it is also possible to carry out theprocess under increased or reduced pressure.

For carrying out process (b) according to the invention, thespecifically required starting substances are generally employed inapproximately equimolar amounts. However, it is also possible to use oneof the two specifically employed components in a substantial excess. Ingeneral, the reactions are carried out in a suitable diluent in thepresence of an acid acceptor, and the reaction mixture is stirred forseveral hours at the specifically required temperature. Working-up inprocess (b) according to the invention is carried out in each case bycustomary methods.

The triazolinones of the formula (II) which are to be used as startingsubstances in process (c) accord-ing to the invention for thepreparation of compounds of the formula (I) have already been describedas starting substances for process (a) according to the invention.

Formula (VI) provides a general definition of the sulphonamidederivatives further to be used as starting substances in process (c)according to the invention for the preparation of compounds of theformula (I).

In formula (VI), R³ and Z preferably, or in particular, have thosemeanings which have already been mentioned above in connection with thedescription of the compounds of the formula (I) or (Iv) according to theinvention as being preferred, particularly preferred, for R³ and Z.

Process (c) according to the invention is preferably carried out usingdiluents. Suitable diluents in this context, are the same organicsolvents as have been mentioned above in connection with the descriptionof process (a) according to the invention.

If appropriate, process (c) is carried out in the presence of an acidacceptor. Suitable acid-binding agents in this context are the same ashave been mentioned above in connection with the description of process(b) according to the invention.

When carrying out process (c) according to the invention the reactiontemperatures can be varied within a substantial range. In general, theprocess is carried out at temperatures between 0° C. and 100° C.,preferably at temperatures between 10° C. and 60° C.

In general, process (c) according to the invention is carried out underatmospheric pressure. However, it is also possible to carry out theprocess under increased or reduced pressure.

For carrying out process (c) according to the invention, thespecifically required starting substances are generally employed inapproximately equimolar amounts. However, it is also possible to use oneof the two specifically employed components in a substantial excess. Ingeneral, the reactions are carried out in a suitable diluent in thepresence of an acid acceptor, and the reaction mixture is stirred forseveral hours at the specifically required temperature. Working-up inprocess (c) according to the in invention is carried out in each case bycustomary methods.

To convert the compounds of the formula (I) into salts, they are stirredwith suitable salt formers, such as, for example, sodium hydroxide,sodium methylate, sodium ethylate, potassium hydroxide, potassiummethylate or potassium ethylate, ammonia, isopropylamine, dibutylamineor triethylamine, using suitable diluents, such as, for example, water,methanol or ethanol. The salts can be isolated as crystalline products--then if appropriate after concentrating the mixture.

The active compounds according to the invention can be used asdefoliants, desiccants, agents for destroying broad-leaved plants and,especially, as weedkillers. By weeds, in the broadest sense, there areto be understood all plants which grow in locations where they areundesired. Whether the substances according to the invention act astotal or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria,Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio,Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum,Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala,Lindernia, Lamium, Veronica, Abutlion, Emex, Datura, Viola, Galeopsis,Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Arena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus andAllium.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The compounds are suitable, depending on the concentration, for thetotal combating of weeds, for example on industrial terrain and railtracks, and on paths and squares with or without tree plantings. Equallythe compounds can be employed for combating weeds in perennial cultures,for example afforestations, decorative tree plantings, orchards,vineyards, citrus groves, nut orchards, banana plantations, coffeeplantations, tea plantations, rubber plantations, oil palm plantations,cocoa plantations, soft fruit plantings and hopfields, in lawns,turf,meadows and pastures, and for the selective combating of weeds inannual cultures.

The compounds of the formula (I) according to the invention are suitablefor combating monocotyledon and dicotyledon weeds both in thepre-emergence and the post-emergence method. They are markedly moreeffective than, for example, isocarbamide.

To a certain extent, the compounds according to the invention also showa fungicidal action, for example against powdery mildews and againstapple scab, and also against Pyricularia oryzae on rice.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusting agents, pastes, soluble powders, granules, suspension-emulsionconcentrates, natural and synthetic materials impregnated with activecompound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surface-active agents, thatis emulsifying agents and/or dispersing agents and/or foam-formingagents.

In the case of the use of water as an extender, organic solvents can,for example, also be used as auxiliary solvents. As liquid solvents,there are suitable in the main: aromatics, such as xylene, toluene, oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol as well as their ethers and esters, ketones, suchas acetone, methyl ethyl ketone, methyl isobuty ketone or cyclohexanone,strongly polar solvents, such as dimethylformamide and dimethylsulphoxide, as well as water,

As solid carriers there are suitable: for example ammonium salts andground natural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as highly disperse silica, alumina and silicates, assolid carriers for granules there are suitable: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepioliteand dolomite, as well as synthetic granules of inorganic and organicmeals, and granules of organic material such as sawdust, coconut shells,maize cobs and tobacco stalks; as emulsifying and/or foam-forming agentsthere are suitable: for example non-ionic and anionic emulsifiers, suchas polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkylary polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates as well as albumen hydrolysis products; asdispersing agents there are suitable: for example lignin-sulphite wasteliquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can bemused in the formulations. Further additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

For combating weeds, the active compounds according to the invention, assuch or in the form of their formulations, can also be used as mixtureswith known herbicides, finished formulations or tank mixes beingpossible.

Suitable herbicides for the mixtures are known herbicides, such as, forexample, 1-amino-6-ethylthio-3-(2,2-dimethylpropyl)-1,3,5-triazine-2, 4(1H, 3H)-dione (AMETHYDIONE) or N-(2-benzothiazolyl)-N,N'-dimethylurea(METABENZTHIAZURON) for combating weeds in cereals;4-amino-3-methyl-6-phenyl-1, 2, 4-triazin-5 (4H)-one (METAMITRON)for-combating weeds in sugar beet and 4-amino-6-(1,1-dimethylethyl)-3methylthio-1,2,4-triazin-5(4H)-one (METRIBUZIN) forcombating weeds in soya beans; furthermore also mixtures with2,4-dichlorophenoxyacetic acid (2,4-D); 4- (2,4-dichlorophenoxy) -butticacid (2,4-DB); 2,4-dichlorophenoxypropionic acid (2,4-DP);5-(2-chloro-4-trifluoromethyl-phenoxy) -2-nitrobenzoic acid(ACIFLUORFEN); 2-chloro-2',6'-diethyl-N-methoxy-methyl-acetanilide(ALACHLOR); 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine(ATRAZINE); methyl 2-[[[[[(4,6-dimethoxypyrimidin-2-yl)-amino]carbonyl]-amino]-sulphonyl]-methyl]-benzoate (BENSULFURON);3-isopropyl-2,1,3-benzothiadiazin-4-one 2,2-dioxide (BENTAZONE); methyl5-(2,4-dichlorophenoxy)-2-nitrobenzoate (BIFENOX);3,5-dibromo-4-hydroxy-benzonitrile; (BROMOXYNIL);N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)-acetamide (BUTACHLOR);ethyl2-{[(4-chloro-6-methoxy-2-pyrimidinyl)-aminocarbonyl]-aminosulphonyl}-benzoate(CHLORIMURON);2-chloro-N-{[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]-carbonyl}-benzenesulphonamid(CHLORSULFURON);N,N-dimethyl-N'-(3-chloro-4-methyl-phenyl)-urea(CHLORTOLURON);2-chloro-4-ethylamino-6-(3-cyanopropylamino)-1,3,5-triazine(CYANAZINE);2,6-dichlorobenzonitrile (DICHLOBENIL);2-[4-(2,4-dichlorophenoxy)-phenoxy]-propionic acid, its methyl ester orits ethyl ester (DICLOFOP);2-[(2-chlorophenyl)-methyl]-4,4-di-methylisoxazolidin-3-one(DIMETHAZONE); 4-amino-6-t-butyl-3-ethylthio-1,2,4-triazin-5(4H)-one(ETHIOZIN); 2-{4-[6-chloro-2-benzoxazolyl)-oxy]-phenoxy}-propanoic acid,its methyl ester or its ethyl ester (FENOXAPROP);2-[4-(5-trifluoromethyl-2-pyridyloxy)-phenoxy]-propanoic acid or itsbutyl ester (FLUAZIFOP); N,N-dimethyl-N' -(3-trifluoromethylphenyl)-urea(FLUOMETURON); 1-methyl-3-phenyl-5-(3-trifluoromethylphenyl)-4-pyridone(FLURIDONE);5-(2-chloro-4-trifluoromethyl-phenoxy)-N-methylsulphonyl-2-nitrobenzamide(FOMSAFEN); N-phos-phonomethyl-glycine (GLYPHOSATE); methyl2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl ]-4(5)-methylbenzoate (IMAZAMETHABENZ);2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-pyridine-3-carboxylic acid (IMAZAPYR);2-[5-methyl-5-(1-methylethyl)-4-oxo-2-imidazolin-2-yl]-3-quinolincarboxylicacid (IMAZAQUIN);2-[4,5-dihydro-4-methyl-4-isopropyl-5-oxo-(1H)-imidazol-2-yl]-5-ethylpyridin-3-carboxylicacid (IMAZETHAPYR); 3,5-diiodo-4-hydroxy-benzonitrile (IOXYNIL);N,N-dimethyl-N'-(4-isopropylphenyl)-urea (ISOPROTURON);(2-methyl-4-chlorophenoxy)-acetic acid (MCPA);(4-chloro-2-methylphenoxy)-propionic acid (MCPP);N-methyl-2-(1,3-benzothiazol-2-yloxy)-acetanilide (MEFENACET);2-chloro-N-(2, 6-dimethyl-phenyl)-N-[(1H)-pyrazol-1-yl-methyl]-acetamide(METAZACHLOR);2-ethyl-6-methyl-N-(1-methyl-2-methoxyethyl)-chloroacetanilide(METOLACHLOR);2-{[[((4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino)-carbonyl]-amino]-sulphonyl}-benzoicaicd or its methyl ester (METSULFURON);1-(3-trifluoromethyl-phenyl)-4-methyamino-5-chloro-6-pyridazone(NORFLURAZON); N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitroaniline(PENDIMETHALIN); 0-(6-chloro-3-phenyl-pyridazin-4-yl) S-octylthiocarbamate (PYRIDATE); ethyl 2-[4-(6-chloro-quinoxalin-2-yl-oxy)-phenoxy]-propionate (QUIZALOFOP-ETHYL); 2-[1-(ethoxamino)-butylidene]-5-(2-ethylthiopropyl)-1,3-cyclohexadione (SETHOXYDIM); methyl2-{[(4,6dimethyl-2-pyrimidinyl)-aminocarbonyl]-aminosulphonyl}-benzoate(SULFOMETURON); 4-ethylamino-2-t-butylamino-6-methylthios-triazine(TERBUTRYNE); methyl 3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]-carbonyl]amino]-sulphonyl]-thiophene-2-carboxylate(THIAMETURON); S-2,3,3-trichloroallyl)-N,N-disopropylthiocarbamate(TRI-ALLATE), 2,6-dinitro-4-trifluoromethyl-N,N-dipropylaniline(TRIFLURALIN). Suprisingly, some mixtures also show a synergisticeffect.

Mixtures with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellants, plant nutrientsand agents which improve soil structure, are also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied eitherbefore or after emergence of the plants.

They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a substantial range.It depends essentially on the nature of the desired effect. In general,the amounts used are between 0.01 and 15 kg of active compound perhectare of soil surface, preferably between 0.05 and 10 kg per ha.

The preparation and use of the active compounds according to theinvention can be seen from the following examples.

PREPARATION EXAMPLES EXAMPLE 1 ##STR290## (Process (a))

3.0 g (17.95 mmol) of4-cyclopentyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one are dissolvedin 60 ml of acetonitrile, and 6.9 g (28.6 mmol) of2-methoxycarbonyl-phenylsulphonyl isocyanate, dissolved in 20 ml ofacetonitrile, are added to this solution with stirring. The reactionmixture is stirred for 6 hours at 20° C. and then concentrated. Theresidue which remains is stirred with diethyl ether, and the productwhich has been obtained in crystalline form is isolated by filtrationwith suction.

This gives 6.6 g (90% of theory) of4-cyclopentyl-5-methyl-2-(2-methoxycarbonyl-phenylsulphonyl-aminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 146° C.

EXAMPLE 2 ##STR291## (Process (b))

1,8 g (11.8 mmol) of 1,8-diazabicyclo-[5,4,0]-undec-7-ene (DBU) areadded to a stirred mixture of 3.0 (12.1 mmol) of5-ethyl-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one,2.5 g (12.2 mmol) of 2-chloro-6-methyl-benzenesulphonamide and 60 ml ofacetonitrile. The reaction mixture is stirred for 2 hours at 20° C.,then poured into about twice the volume of ice-water, and a pH of about2 is established by dropwise addition of concentrated hydrochloric acid.The product which has been obtained during this process in crystallineform is isolated by filtration with suction.

This gives 3.2 g (73.5% of theory) of5-ethyl-4-methyl-2-(2-chloro-6-methyl-phenylsulphonyl-aminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 176° C.

For example the compounds of the formula (I) listed in Table 3 below canalso be prepared analogously to Examples 1 and 2 and following thegeneral instructions of the preparation processes according to theinvention.

                                      TABLE 3                                     __________________________________________________________________________     ##STR292##                             (I)                                   Preparation Examples of the compounds of the formula (1) (m.p. = melting      point):                                                                       Ex.                                                                           No.                                                                              R.sup.1    R.sup.2  R.sup.3      m.p. (°C.)                         __________________________________________________________________________     3 C.sub.6 H.sub.5                                                                          CH.sub.3                                                                                ##STR293##  158                                        4 CH.sub.3   C.sub.2 H.sub.5                                                                         ##STR294##  159                                        5 C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                         ##STR295##  115                                        6 CH.sub.3   C.sub.3 H.sub.7                                                                         ##STR296##  143                                        7 C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                         ##STR297##  139                                        8 CH.sub.3   C.sub.3 H.sub.7                                                                         ##STR298##  141                                        9 OCH.sub.3  CH.sub.3                                                                                ##STR299##  121                                       10 OCH.sub.3  CH.sub.3                                                                                ##STR300##  180                                       11 OCH.sub.3  CH.sub.3                                                                                ##STR301##  149                                       12 OCH.sub.3  C.sub.2 H.sub.5                                                                         ##STR302##  144                                       13 OCH.sub.3  C.sub.3 H.sub.7                                                                         ##STR303##  128                                       14 CH.sub.3   C.sub.2 H.sub.5                                                                         ##STR304##  173                                       15 CH.sub.3   C.sub.3 H.sub.7                                                                         ##STR305##  133                                       16                                                                                ##STR306##                                                                              C.sub.2 H.sub.5                                                                         ##STR307##  154                                       17 OCH.sub.3  CH(CH.sub.3).sub.2                                                                      ##STR308##  137                                       18                                                                                ##STR309##                                                                              C.sub.2 H.sub.5                                                                         ##STR310##  174                                       19                                                                                ##STR311##                                                                              C.sub.3 H.sub.7                                                                         ##STR312##   97                                       20 CH.sub.3   N(CH.sub.3).sub.2                                                                       ##STR313##  168                                       21 OCH.sub.2 C.sub.6 H.sub.5                                                                CH.sub.3                                                                                ##STR314##  174                                       22 C.sub.2 H.sub.5                                                                          C.sub.3 H.sub.7                                                                         ##STR315##  136                                       23 N(CH.sub.3).sub.2                                                                        C.sub.2 H.sub.5                                                                         ##STR316##  139                                       24 N(CH.sub.3).sub.2                                                                        H                                                                                       ##STR317##  197                                       25 N(CH.sub.3).sub.2                                                                        CH(CH.sub.3).sub.2                                                                      ##STR318##  148                                       26 OC.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                         ##STR319##  153                                       27 OC.sub.2 H.sub.5                                                                         C.sub.3 H.sub.7                                                                         ##STR320##  155                                       28                                                                                ##STR321##                                                                              CH(CH.sub.3).sub.2                                                                      ##STR322##  186                                       29                                                                                ##STR323##                                                                              C.sub.3 H.sub.7                                                                         ##STR324##  146                                       30 N(CH.sub.3).sub.2                                                                        C.sub.3 H.sub.7                                                                         ##STR325##  110                                       31 N(CH.sub.3).sub.2                                                                         ##STR326##                                                                             ##STR327##  131                                       32 C.sub.2 H.sub.5                                                                          C.sub.4 H.sub.9                                                                         ##STR328##   98                                       33 CH.sub.3   C.sub.4 H.sub.9                                                                         ##STR329##  113                                       34 C.sub.3 H.sub.7                                                                          C.sub.4 H.sub.9                                                                         ##STR330##   88                                       35                                                                                ##STR331##                                                                              C.sub.4 H.sub.9                                                                         ##STR332##  117                                       36 OCH.sub.3  C.sub.4 H.sub.9                                                                         ##STR333##  117                                       37 CH.sub.3                                                                                  ##STR334##                                                                             ##STR335##  141                                       38 C.sub.2 H.sub.5                                                                           ##STR336##                                                                             ##STR337##  130                                       39 C.sub.3 H.sub.7                                                                           ##STR338##                                                                             ##STR339##  139                                       40                                                                                ##STR340##                                                                               ##STR341##                                                                             ##STR342##  151                                       41                                                                                ##STR343##                                                                              CH.sub.3                                                                                ##STR344##  151                                       42 CH(CH.sub.3).sub.2                                                                       NHCH(CH.sub.3).sub.2                                                                    ##STR345##  135                                       43 N(CH.sub.3).sub.2                                                                        N(CH.sub. 3).sub.2                                                                      ##STR346##  171                                       44 CH.sub.3   C.sub.3 H.sub.7                                                                         ##STR347##  168                                       45 C.sub.2 H.sub.5                                                                          N(CH.sub.3).sub.2                                                                       ##STR348##  134                                       46 CH.sub.3   C.sub.2 H.sub.5                                                                         ##STR349##  167                                       47 NH.sub.2   C.sub.3 H.sub.7                                                                         ##STR350##  120                                       48                                                                                ##STR351##                                                                               ##STR352##                                                                             ##STR353##  120                                       49                                                                                ##STR354##                                                                              H                                                                                       ##STR355##  195                                       50 CH.sub.2 CHCH.sub.2                                                                      C.sub.2 H.sub.5                                                                         ##STR356##  108                                       51 CH.sub.2 CHCH.sub.2                                                                      H                                                                                       ##STR357##  158                                       52 OCH.sub.3  C.sub.3 H.sub.7                                                                         ##STR358##  110-111                                   53                                                                                ##STR359##                                                                              H                                                                                       ##STR360##  212-214                                   54 C.sub.3 H.sub.7                                                                          H                                                                                       ##STR361##  168-169                                   55                                                                                ##STR362##                                                                              C.sub.3 H.sub.7                                                                         ##STR363##  103-105                                   56                                                                                ##STR364##                                                                              C.sub.2 H.sub.5                                                                         ##STR365##  127                                       57 OCH.sub.3  C.sub.2 H.sub.5                                                                         ##STR366##  111-113                                   58 OCH.sub.3                                                                                 ##STR367##                                                                             ##STR368##  139                                       59 NHCH.sub.3 C.sub.3 H.sub.7 -n                                                                      ##STR369##  196                                       60 CH.sub.3   C.sub.3 H.sub.7 -n                                                                      ##STR370##  178                                       61                                                                                ##STR371##                                                                              H                                                                                       ##STR372##  177                                       62 CH.sub.2 CH(CH.sub.3).sub.2                                                              C.sub.2 H.sub.5                                                                         ##STR373##  123                                       63 CH.sub.2CHCH.sub.2                                                                       C.sub.3 H.sub.7 -n                                                                      ##STR374##  (amorphous)                               64                                                                                ##STR375##                                                                              C.sub.2 H.sub.5                                                                         ##STR376##  157                                       65                                                                                ##STR377##                                                                              C.sub.2 H.sub.5                                                                         ##STR378##  117                                       66 C(CH.sub.3).sub.3                                                                        C.sub.2 H.sub.5                                                                         ##STR379##  182                                       67                                                                                ##STR380##                                                                              C.sub.2 H.sub.5                                                                         ##STR381##  133                                       68                                                                                ##STR382##                                                                              C.sub.2 H.sub.5                                                                         ##STR383##  162                                       69 CH.sub.2CHCH.sub.2                                                                       CH.sub.3                                                                                ##STR384##  120                                       70                                                                                ##STR385##                                                                              C.sub.2 H.sub.5                                                                         ##STR386##  183                                       71 C.sub.2 H.sub.5                                                                          H                                                                                       ##STR387##  196                                       72                                                                                ##STR388##                                                                              CH.sub.3                                                                                ##STR389##  153                                       73 OCH.sub.3                                                                                 ##STR390##                                                                             ##STR391##  138                                       74 CH(CH.sub.3).sub.2                                                                       H                                                                                       ##STR392##  191                                       75                                                                                ##STR393##                                                                              H                                                                                       ##STR394##  191                                       76                                                                                ##STR395##                                                                              H                                                                                       ##STR396##  192                                       77 C(CH.sub.3).sub.3                                                                        H                                                                                       ##STR397##  211                                       78                                                                                ##STR398##                                                                              CH.sub.3                                                                                ##STR399##  110                                       79 CH.sub.3   CH.sub.2 OCH.sub.3                                                                      ##STR400##  152                                       80 CH.sub.3   C.sub.2 H.sub.5                                                                         ##STR401##  174                                       81 CH.sub.3   CH.sub.2 OC.sub.2 H.sub.5                                                               ##STR402##  123                                       82 OCH.sub.3  C.sub.3 H.sub.7 -n                                                                      ##STR403##  (amorphous)                               83                                                                                ##STR404##                                                                              C.sub.2 H.sub.5                                                                         ##STR405##  124                                       84                                                                                ##STR406##                                                                              CH.sub.2 OCH.sub.3                                                                      ##STR407##  102                                       85                                                                                ##STR408##                                                                              CH.sub.2 OCH.sub.3                                                                      ##STR409##  155                                       86                                                                                ##STR410##                                                                              CH.sub.2 OC.sub.2 H.sub.5                                                               ##STR411##  123                                       87                                                                                ##STR412##                                                                              CH.sub.2 OC.sub.2 H.sub. 5                                                              ##STR413##   99                                       88                                                                                ##STR414##                                                                              N(CH.sub.3).sub.2                                                                       ##STR415##  189                                       89 OCH.sub.3  C.sub.2 H.sub.5                                                                         ##STR416##  155                                       90                                                                                ##STR417##                                                                              C.sub.2 H.sub.5                                                                         ##STR418##  133                                       91 OCH.sub.3  C.sub.3 H.sub.7 -n                                                                      ##STR419##  125                                       92                                                                                ##STR420##                                                                              C.sub.2 H.sub.5                                                                         ##STR421##  138                                       93 OC.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                         ##STR422##  132                                       94 OC.sub.2 H.sub.5                                                                         C.sub.3 H.sub.7 -n                                                                      ##STR423##  107                                       95 OCH.sub.3  CH(CH.sub. 3).sub.2                                                                     ##STR424##  128                                       96 OCH.sub.3  CH.sub.3                                                                                ##STR425##  119                                       97                                                                                ##STR426##                                                                              C.sub.3 H.sub.7 -n                                                                      ##STR427##  100                                       98                                                                                ##STR428##                                                                               ##STR429##                                                                             ##STR430##  140                                       99                                                                                ##STR431##                                                                              N(CH.sub.3).sub.2                                                                       ##STR432##  163                                       100                                                                               ##STR433##                                                                              N(CH.sub.3).sub.2                                                                       ##STR434##  182                                       101                                                                              CH.sub.3   N(CH.sub.3).sub.2                                                                       ##STR435##  181                                       102                                                                              CH.sub.3   OCH.sub.3                                                                               ##STR436##  150                                       103                                                                              C.sub.2 H.sub.5                                                                           ##STR437##                                                                             ##STR438##  147                                       104                                                                              CH.sub.2CHCH.sub.2                                                                       CH.sub.3                                                                                ##STR439##  132                                       105                                                                              CH.sub.2CHCH.sub.2                                                                       C.sub.2 H.sub.5                                                                         ##STR440##  109                                       106                                                                              CH.sub.2CHCH.sub.2                                                                       C.sub.3 H.sub.7 -n                                                                      ##STR441##  104                                       107                                                                              OC.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                         ##STR442##  147                                       108                                                                              OC.sub.2 H.sub.5                                                                         C.sub.3 H.sub.7 -n                                                                      ##STR443##  136                                       109                                                                              OCH.sub.3  CH(CH.sub.3).sub.2                                                                      ##STR444##  126                                       110                                                                              CH.sub.3   CH.sub.3                                                                                ##STR445##  146                                       111                                                                               ##STR446##                                                                              CH.sub.3                                                                                ##STR447##  175                                       112                                                                              CH.sub.3   CH(CH.sub.3).sub.2                                                                      ##STR448##  124                                       113                                                                              CH.sub.3                                                                                  ##STR449##                                                                             ##STR450##  171                                       114                                                                               ##STR451##                                                                              CH(CH.sub.3).sub.2                                                                      ##STR452##  132                                       115                                                                               ##STR453##                                                                               ##STR454##                                                                             ##STR455##  167                                       116                                                                              CH.sub.3   CH.sub.3                                                                                ##STR456##  155                                       117                                                                              CH.sub.3   C.sub.2 H.sub.5                                                                         ##STR457##  147                                       118                                                                              CH.sub.3   C.sub.3 H.sub.7 -n                                                                      ##STR458##  169                                       119                                                                              OCH.sub. 3 C.sub.2 H.sub.5                                                                         ##STR459##                                            120                                                                               ##STR460##                                                                              C.sub.2 H.sub.5                                                                         ##STR461##  132                                       __________________________________________________________________________

EXAMPLE 121 ##STR462##

A mixture of 3.8 g (0.03 mol) of 5-ethyl-4-methyl-2, 4-dihydro-3H-1, 2,4triazol-3-one, 12 g (0.05mol) of 2-methoxy-carbonyl-phenylsulphonyisocyanate and 50 ml of methylene chloride is stirred at 20° C. for 20hours and then evaporaetd under a waterpump vacuum. The residue istriturated with diethyl ether, and the crystalline product which isobtained during this process is isolated by filtering off with suction.

6 g (54% of theory) of5-ethyl-4methyl-2-(2-methoxycarbonyl-phenylsulphonyl-aminocaebonyl)-2,4-dihydro-3H-1,2, 4-triazol-3-one of melting point 131° C. are obtained.

In analogy to Example 121 and following the general description of thepreparation process according to the invention, for example thecompounds of the formula (I) which are listed in Table 3 below can beprepared.

                                      TABLE 3 - continuation                      __________________________________________________________________________     ##STR463##                         (I)                                       Ex.                                                                           No. R.sup.1   R.sup.2  R.sup.3   m.p. (°C.)                            __________________________________________________________________________    122 C.sub.2 H.sub.5                                                                         H                                                                                       ##STR464##                                                                             118                                          123 CH.sub.3  CH.sub.3                                                                                ##STR465##                                                                             172                                          124 CH.sub.3  C.sub.2 H.sub.5                                                                         ##STR466##                                                                             122                                          125 CH.sub.3  CH.sub.2 CH.sub.2 OCH.sub.3                                                             ##STR467##                                                                             amorphous                                    126 CH.sub.3  C.sub.2 H.sub.5                                                                         ##STR468##                                                                             164                                          127 C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                         ##STR469##                                                                             172                                          128 CH.sub.3  C.sub.3 H.sub.7 -n                                                                      ##STR470##                                                                             132                                          129 C.sub.2 H.sub.5                                                                         C.sub.3 H.sub.7 -n                                                                      ##STR471##                                                                             153                                          130 CH(CH.sub.3).sub.2                                                                      C.sub.3 H.sub.7 -n                                                                      ##STR472##                                                                             157                                          131 CH.sub.3  C.sub.2 H.sub.5                                                                         ##STR473##                                                                             200                                          132 C.sub.2 H.sub.5                                                                         CH.sub.3                                                                                ##STR474##                                                                             173                                          133 C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                         ##STR475##                                                                             207                                          134 CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                                ##STR476##                                                                             127                                          135 CH(CH.sub.3).sub.2                                                                      CH(CH.sub.3).sub.2                                                                      ##STR477##                                                                             142                                          136 CH(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                                                         ##STR478##                                                                             112                                          137 CH.sub.3  CH(CH.sub.3).sub.2                                                                      ##STR479##                                                                             125                                          138 C.sub.2 H.sub.5                                                                         CH(CH.sub.3).sub.2                                                                      ##STR480##                                                                             250                                          139 C.sub.3 H.sub.7 -n                                                                      CH(CH.sub.3).sub.2                                                                      ##STR481##                                                                             255                                          140 CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                                ##STR482##                                                                             165                                          141 C.sub.3 H.sub.7                                                                         CH.sub.3                                                                                ##STR483##                                                                             180                                          142 C.sub.3 H.sub.7 -n                                                                      C.sub.2 H.sub.5                                                                         ##STR484##                                                                             187                                          143 CH(CH.sub.3).sub.2                                                                      C.sub.2 H.sub.5                                                                         ##STR485##                                                                             133                                          144 CH.sub.3  C.sub.3 H.sub.7 -n                                                                      ##STR486##                                                                             225                                          145 C.sub.2 H.sub.5                                                                         C.sub.3 H.sub.7 -n                                                                      ##STR487##                                                                             173                                          146 C.sub.3 H.sub.7 -n                                                                      C.sub.3 H.sub.7 -n                                                                      ##STR488##                                                                             143                                          147 CH(CH.sub.3).sub.2                                                                      C.sub.3 H.sub.7 -n                                                                      ##STR489##                                                                             120                                          148 CH.sub.3  CH(CH.sub.3).sub.2                                                                      ##STR490##                                                                             147                                          149 C.sub.2 H.sub.5                                                                         CH(CH.sub.3).sub.2                                                                      ##STR491##                                                                             187                                          150 C.sub.3 H.sub.7 -n                                                                      CH(CH.sub.3).sub.2                                                                      ##STR492##                                                                              78                                          151 CH(CH.sub.3).sub.2                                                                      CH(CH.sub.3).sub.2                                                                      ##STR493##                                                                             167                                          152 CH.sub.3  C.sub.2 H.sub.5                                                                         ##STR494##                                                                             144                                          153 CH.sub.3  CH.sub.3                                                                                ##STR495##                                                                             133                                          154 C.sub.2 H.sub.5                                                                         CH.sub.3                                                                                ##STR496##                                                                             141                                          155                                                                                ##STR497##                                                                             CH.sub.3                                                                                ##STR498##                                                                             144                                          156                                                                                ##STR499##                                                                             CH.sub.3                                                                                ##STR500##                                                                             173                                          157 N(CH.sub.3).sub.2                                                                       CH.sub.3                                                                                ##STR501##                                                                             165                                          __________________________________________________________________________

STARTING SUBSTANCES OF THE FORMULA (II) EXAMPLE (II-1) ##STR502## Step1: ##STR503##

A mixture of 68.5 g (0.60 mol) of 5-methyl-l,3,4-oxadiazolin-2-one, 45.8g (0.75 mol) of 0-ethyl-hydroxylamine and 400 ml of water is refluxedfor 12 hours and then concentrated. The residue is taken up in ethanoland reconcentrated. The residue which is obtained in this process isstirred with diethyl ether, and the product which has been obtained incrystalline form is isolated by filtration with suction. This gives 77.5g (74% of theory) of 1-ethoxyaminocarbonyl-2-propionyl-hydrazine ofmelting point 122° C.

Step 2 ##STR504##

A mixture of 75.5 g (0.43 mol) of1-ethoxyaminocarbonyl-2-propionyl-hydrazine, 17.5 g (0.44 mol) of sodiumhydroxide and 300 ml of water is refluxed for 12 hours. When the mixtureis cold, a ph of between 3 and 4 is established by adding concentratedhydrochloric acid, and the mixture is concentrated. The residue isstirred with ethyl acetate, and the sodium chloride which has remainedundissolved is separated off by filtration with suction. The filtrate isconcentrated, the residue is stirred with diethyl ether, and the productwhich has been obtained in crystalline form is isolated by filtrationwith suction.

This gives 37 g (55% of theory) of4-ethoxy-5-ethyl-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 93°C.

EXAMPLE (II-2) ##STR505##

A mixture of 40 g (0.31 mol) of 5-propyl-1,3,4-oxadiazolin-2-one, 109 gof aqueous methylamine solution (32% strength, 1.125 mol of CH₃ NH₂) and500 ml of water is refluxed for 12 hours and then concentrated. Theresidue is taken up in ethanol and reconcentrated. The residue obtainedin this process is stirred with diethyl ether, and the product which hasbeen obtained in crystalline form is isolated by filtration withsuction.

This gives 31.7 g (72% of theory) of4-methyl-5-propyl-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point86° C.

EXAMPLE (II-3) ##STR506##

856 g (4.0 mol) of diphenyl carbonate are dissolved in 588 g of ethylenechloride. 245 g (4.0 mol) of dimethyhydrazine (98% pure) are addeddropwise with water-cooling, and the mixture is heated slowly and, for 4hours, stirred at 60° C.

After the mixture has cooled to 20° C., 200 g (4.0 mol) of hydrazinehydrate are added dropwise, and the mixture is then stirred for 12hours. It is warmed to 70°-80° C. and, for about 1 hour, stirring iscontinued. when cold, the solution is distilled in vacuo, during whichprocess ethylene chloride and water are removed (final bottomtemperature 100° C.). The above phenolic dimethyl carbodihydrazidesolution is added dropwise in the course of 90 minutes at refluxtemperature (about 102° C.) to 424 g (4.0 mol) of trimethylorthoformate. After the methanol which has formed is removed bydistillation, phenol is distilled off in vacuo, after which 282 g ofproduct mixture are obtained at a head temperature of 85°-105° C. Thismixture is boiled with 600 ml of acetone, and filtered at boiling point,and the filtrate is then cooled. The product which has been obtained inthis process in crystalline form is isolated by filtration with suction.

This gives 71 g (14% of theory) of4-dimethylamino-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 127°C.

For example the compounds of the formulae (II) and (IIa) listed in Table4 below can also be prepared analogously to Examples (II-1) to (II3).

                  TABLE 4                                                         ______________________________________                                         ##STR507##                  (II)                                             Preparation examples of the compounds of the                                  formula (II)                                                                  Ex.                                 m.p.                                      No.   R.sup.1          R.sup.2      (°C.)                              ______________________________________                                        II-4  C.sub.3 H.sub.7  CH.sub.3      48                                       II-5  CH(CH.sub.3).sub.2                                                                             CH.sub.3     118                                       II-6  CH.sub.3         CH.sub.3     139                                       II-7  C.sub.2 H.sub.5  C.sub.2 H.sub.5                                                                            117                                       II-8  C.sub.3 H.sub.7  C.sub.2 H.sub.5                                                                             42-45                                    II-9  CH(CH.sub.3).sub.2                                                                             C.sub.2 H.sub.5                                                                            102                                       II-10 C.sub.2 H.sub.5  C.sub.3 H.sub.7                                                                             97                                       II-11 C.sub.3 H.sub.7  C.sub.3 H.sub.7                                                                            (amor-                                                                        phous)                                    II-12 CH(CH.sub.3).sub.2                                                                             C.sub.3 H.sub.7                                                                             91                                       II-13 CH.sub.3         CH(CH.sub.3).sub.2                                                                          92                                       II-14 C.sub.2 H.sub.5  CH(CH.sub.3).sub.2                                                                         (amor-                                                                        phous)                                    II-15 C.sub.3 H.sub.7  CH(CH.sub.3).sub.2                                                                         (amor-                                                                        phous)                                    II-16 CH(CH.sub.3).sub.2                                                                             CH(CH.sub.3).sub.2                                                                         168                                       II-17 C.sub.2 H.sub.5  CH.sub.3     134                                       II-18                                                                                ##STR508##      CH.sub.3     159                                       II-19 OCH.sub.3        CH.sub.3     178                                       II-20 OCH.sub.3        C.sub.2 H.sub.5                                                                            140                                       II-21 OCH.sub.3        C.sub.3 H.sub.7                                                                            127                                       II-22 OCH.sub.3        CH(CH.sub.3).sub.2                                                                         130                                       II-23 OCH.sub.2 C.sub.6 H.sub.5                                                                      CH.sub.3     106                                       II-24                                                                                ##STR509##      C.sub.2 H.sub.5                                                                            150                                       II-25                                                                                ##STR510##      C.sub.3 H.sub.7                                                                            130                                       II-26 OC.sub.2 H.sub.5 C.sub.3 H.sub.7                                                                             72                                       II-27                                                                                ##STR511##      CH(CH.sub.3).sub.2                                                                         121                                       II-28 CH.sub.3         C.sub.4 H.sub.9                                                                             50                                       II-29 C.sub.2 H.sub.5  C.sub.4 H.sub.9                                                                             76                                       II-30 C.sub.3 H.sub.7  C.sub.4 H.sub.9                                                                            (amor-                                                                        phous)                                    II-31 OCH.sub.3        C.sub.4 H.sub.9                                                                            100                                       II-32                                                                                ##STR512##      C.sub.4 H.sub.9                                                                             66                                       II-33 CH.sub.3                                                                                        ##STR513##   68                                       II-34 C.sub.2 H.sub.5                                                                                 ##STR514##  130                                       II-35 C.sub.3 H.sub.7                                                                                 ##STR515##   68                                       II-36                                                                                ##STR516##                                                                                     ##STR517##  154                                       II-37 N(CH.sub.3).sub.2                                                                              CH.sub.3     153                                       II-38 N(CH.sub.3).sub.2                                                                              C.sub.2 H.sub.5                                                                            114                                       II-39 N(CH.sub.3).sub.2                                                                              C.sub.3 H.sub.7                                                                            108                                       II-40 N(CH.sub.3).sub.2                                                                              CH(CH.sub.3).sub.2                                                                         100                                       II-41 CH.sub.3         N(CH.sub.3).sub.2                                                                           80                                       II-42 N(CH.sub.3).sub.2                                                                               ##STR518##  134                                       II-43 CH(CH.sub.3).sub.2                                                                             NHCH(CH.sub.3).sub.2                                                                       205                                       II-44 N(CH.sub.3).sub.2                                                                              N(CH.sub.3).sub.2                                                                           93                                       II-45 C.sub.2 H.sub.5  N(CH.sub.3).sub.2                                                                           50                                       II-46                                                                                ##STR519##      CH.sub.3     145                                       II-47                                                                                ##STR520##      CH.sub.3     163                                       II-48                                                                                ##STR521##      H            102                                       II-49 OCH.sub.3                                                                                       ##STR522##  136-137                                   II-50 CH.sub.3         C.sub.6 H.sub.5                                        II-51 NH.sub.2         H            192                                       II-52 NH.sub.2         CH.sub.3     230                                       II-53 NH.sub.2         CF.sub.3     163                                       II-54 NHCH.sub.3       CH(CH.sub.3).sub.2                                                                         205                                       II-55 NHCH.sub.3                                                                                      ##STR523##   95                                       II-56 NH.sub.2         C.sub.2 H.sub.5                                                                            170                                       II-57 NH.sub.2         C.sub.3 H.sub.7                                                                            147                                       II-58 NHCH.sub.3       NHCH.sub.3   137                                       II-59 CH.sub.2 C.sub.6 H.sub.5                                                                       C.sub.2 H.sub.5                                                                            125                                       II-60 NHCH.sub.3       H            133                                       II-61 NHCH.sub.3       N(CH.sub.3).sub.2                                                                          129                                       II-62 NHCH.sub.3       C.sub.3 H.sub.7                                                                             76                                       II-63 NH.sub.2                                                                                        ##STR524##  248                                       II-64 NH.sub.2                                                                                        ##STR525##  176                                       II-65 NH.sub.2                                                                                        ##STR526##  183                                       II-66 NH.sub.2                                                                                        ##STR527##  210                                       II-67 NHCH.sub.3       C.sub.2 H.sub.5                                                                            101                                       II-68 NH.sub.2         N(C.sub.2 H.sub.5).sub.2                                                                   196                                       II-69 NH.sub.2                                                                                        ##STR528##  233                                       II-70 NH.sub.2         CH(CH.sub.3).sub.2                                                                         172                                       II-71 NH.sub.2         C(CH.sub.3).sub.3                                                                          261                                       II-72 NH.sub.2         CH.sub.2 CH.sub.2 OCH.sub.3                                                                 98                                       II-73 NH.sub.2         C(CH.sub.3).sub.2 C.sub.2 H.sub.5                                                          213                                       II-74 NH.sub.2         NHC.sub.2 H.sub.5                                                                          220                                       II-75 NH.sub.2         OCH.sub.3    (amor-                                                                        phous)                                    II-76 NH.sub.2         CH.sub.2 OCH.sub.3                                                                         134                                       II-77 NH.sub.2         CH.sub.2 OC.sub.2 H.sub.5                                                                  104                                       II-78 N(CH.sub.3).sub.2                                                                              CH.sub.3     153                                       II-79                                                                                ##STR529##      C.sub.2 H.sub.5                                                                            103                                       II-80 CH.sub.2 CH(CH.sub.3).sub.2                                                                    C.sub.2 H.sub.5                                                                            105                                       II-81 C.sub.6 H.sub.5  H            183                                       II-82 N(CH.sub.3).sub.2                                                                              CH(CH.sub.3).sub.2                                                                         (amor-                                                                        phous)                                    II-83 NHCH.sub.3       CH.sub.3     114                                       II-84 NH.sub.2         CH.sub.2 C.sub.6 H.sub.5                                                                   168                                       II-85 NH.sub.2         N(CH.sub.3).sub.2                                                                          207                                       II-86 NH.sub.2         C.sub.6 H.sub.5                                                                            230                                       II-87 NH.sub.2                                                                                        ##STR530##  223                                       II-88 NH.sub.2         NHCH(CH.sub.3).sub.2                                                                       152                                       II-89 NHCH.sub.3       NHCH(CH.sub.3).sub.2                                                                       120                                       II-90                                                                                ##STR531##                                                                                     ##STR532##  254                                       II-91                                                                                ##STR533##      N(CH.sub.3).sub.2                                      II-92 CH.sub.2 C.sub.6 H.sub.5                                                                       H            111                                       II-93 C.sub.3 H.sub.7  H             48                                       II-94 C.sub.6 H.sub.5  C.sub.2 H.sub.5                                                                            124                                       II-95 C(CH.sub.3).sub.3                                                                              C.sub.2 H.sub.5                                                                            158                                       II-96 CH.sub.3         H            157                                       II-97                                                                                ##STR534##      C.sub.2 H.sub.5                                                                            108                                       II-98                                                                                ##STR535##      C.sub.2 H.sub.5                                                                            132                                       II-99 CH.sub.2 CHCH.sub.2                                                                            CH.sub.3     108                                       II-100                                                                              C.sub.6 H.sub.5  CH.sub.3     150                                       II-101                                                                               ##STR536##      CH.sub.3     116                                       II-102                                                                               ##STR537##      C.sub.2 H.sub.5                                                                            146                                       II-103                                                                              C.sub.2 H.sub.5  H             68                                       II-104                                                                              CH(CH.sub.3).sub.2                                                                             H            105                                       II-105                                                                               ##STR538##      H             79                                       II-106                                                                               ##STR539##      H            162                                       II-107                                                                              C(CH.sub.3).sub.3                                                                              H            194                                       II-108                                                                               ##STR540##      CH.sub.3     111                                       II-109                                                                              CH.sub.3         CH.sub.2 OCH.sub.3                                                                         104                                       II-110                                                                              CH.sub.3         CH.sub.2 OC.sub.2 H.sub.5                                                                  102                                       II-111                                                                               ##STR541##      CH.sub.2 OCH.sub.3                                                                         102                                       II-112                                                                               ##STR542##      CH.sub.2 OC.sub.2 H.sub.5                                                                  119                                       II-113                                                                               ##STR543##      N(CH.sub.3).sub.2                                                                          130                                       II-114                                                                              NH.sub.2                                                                                        ##STR544##  186                                       II-115                                                                              NH.sub.2                                                                                        ##STR545##  165                                       II-116                                                                              NH.sub.2                                                                                        ##STR546##  186                                       II-117                                                                              NH.sub.2                                                                                        ##STR547##  267                                       II-118                                                                              CH.sub.3         OCH.sub.3    144                                       ______________________________________                                    

The compound of Example (II118) disclosed in Table 4 (above) can beprepared as follows: ##STR548## 50.2 g (0.33 mol) of hydrazino-formicacid phenyl ester (═1-phenoxycarbonyl-hydrazine) and 36.6 g (0.33 mol;90% purity) of O,O,N-trimetbyl-iminocarbonate are mixed at 40° C. with100 ml of 1,2-dichlorobenzene, and this mixture is then stirred for twohours at 60° C. Thereafter the mixture is heated further up to 120° C.,while methanol (formed during the reaction) is being distilled off. Thenthe reaction mixture is cooled and heated again in vacuo (0,01 mbar) toa temperature of 120° C. in order

to remove any remaining volatile compounds (methanol, phenol and1,2-dichlorobenzene) from the reaction mixture. At a temperature above120° C. the reaction product is distilled roughly and then crystallizedfrom toluene.

This gives 7.5 g (18% of theory) of5-methoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-one as colorlesscrystals of melting point 144 ° C.

EXAMPLE (II-119) ##STR549##

57 g (1 mol) of methyl isocyanate are added drop-wise at 20° C. to 30°C. to stirred mixture of 50 g (1 mol) of hydrazine hydrate and 200 ml ofwater; the reaction mixture is stirred for 2 hours at 20° C. to 30° C.,and the solvent is then carefully distilled off under a waterpumpvacuum.

The resulting methylaminocarbonylhydrazine (H₂ N-NH-CO-NHCH₃) - 82.5 g(0.93 mol) - is taken up in 800 ml of methylene chloride, and 114 g(0.88 mol) of propionic anhydride are added dropwise at 20° C. to 30° C.to the stirred mixture. The reaction mixture is refluxed for 30 minutesand then stirred at 20° C. for 15 hours. The product which is obtainedin the form of crystals is isolated by filtering off with suction.

The resulting N-methyleminocarbonyl-N'-propionylhydrazine (H₅ C₂-CO-NH-NH-CO-NHCH₃) - 114 g (0.79 mol) -is added to a solution of 31.4 g(0.79 mol) of sodium hydroxide in 2.4 l of water and the reactionmixture is stirred at 90° C. for 60 minutes. The mixture is thenevaporated, the residue is stirred with 300 ml of ethanol/ethyl acetate,and the mixture is filtered. The filtrate is concentrated and stirredwith diethyl ether, and the product which is obtained in the form ofcrystals in this process is isolated by filtering off with suction.

67.4 g (67% of theory) of5-ethyl-4-methyl-2,4-dihydro-3H-2,4-triazol-3-one of melting point 86°C. are obtained.

STARTING SUBSTANCES OF THE FORMULA (III) EXAMPLE (III-1)

900 g (5.1 mol) of 2-trilfluoromethoxy-toluene(2-methyl-trifluoroanisole) are heated at 100° C., and 180 g (2.54 mol)of chlorine are passed in at this temperature and with UV irradiation.Nitrogen is then blown in, and the reaction mixture is subjected tofractional distillation under reduced pressure.

As the main fraction, 425 g (40% of theory) of 2-trifluoromethoxy-benzylchloride (2-chloromethyl-trifluoroanisole) of boiling point 110° C./100°mbar and of refractive index n_(D) ²⁰ =1.5450 are obtained.

21.0 g (0.1 mol) of 2-trifluoromethoxy-benzyl chloride and a saturatedsolution of 13.9 g (0.11 mol) of sodium sulphite in water are refluxedfor 5 hours with vigorous stirring. After cooling, the precipitatedwhite solids are filtered off with suction and rinsed with a smallamount of ice-cold water,

After drying over phosphorus pentoxide, 26.4 g (95% of theory) of sodium2-trifluoromethoxy-benzylsulphonate of melting point 115° C. areobtained.

23.7 g (0.085 mol) of sodium 2-trifluoromethoxybenzylsulphonate aremixed with 35.5 g (0.17 mol) of phosphorus pentachloride, and themixture is swirled for approx. 2 hours on a rotary evaporator at 80°C.-90° C. bath temperature. The mixture is cooled, and the phosphorusoxychloride which has formed is removed in vacuo. The residue issuspended in methylene chloride, and the mixture is poured into icewater. The organic phase is separated off, washed to neutrality, driedand concentrated.

19.0 g (81.4% of theory) of 2-trifluoromethoxybenzylsulphonyl chlorideare obtained as a crude product which is sufficiently pure for thesubsequent reaction to give the sulphonamide. For purification, thecrude product can be taken up in methylene chloride and purified oversilica gel: n_(D) ²².5 =1.4854.

205.9 g (0.75 mol) of 2-trifluoromethoxy-benzylsulphonyl chloride areintroduced at 30° C.-40° C. into 1.5 l of a saturated aqueous ammoniasolution, and the mixture is subsequently stirred at 50° C. -60° C. for3 hours.

After cooling, the precipitated solids are filtered off with suction,washed to neutrality with water and dried.

136.5 g (71% of theory) of 2-trifluoromethoxybenzylsulphonamide ofmelting point 127° C. are obtained.

A mixture of 8.9 g (0.035 mol) of 2-trifluoromethoxybenzylsulphonamide,3.5 g (0.035 mol) of n-butyl isocyanate, 0.2 g ofdiaza-bicyclo-[2.2.2]-octane (DABCO) and 150 ml of anhydrous xylene isheated at reflux temperature and a weak stream of phosgene is passed infor two hours. The mixture is subsequently stirred under refluxconditions for 30 minutes, then cooled, filtered and evaporated. Theresidue is taken up in methylene chloride and refiltered. The liltratecontains 2-trifluoromethoxy-benzylsulphonyl isocyanate as a crudeproduct in a mixture with DABCO and is used further as such for thesubsequent reaction since partial decomposition occurs on high-vacuumdistillation.

Examples of hydrazine derivatives of the formula (IX) which can beobtained analogously to Example (II-1), step 1 , are listed in Table 5below.

                  TABLE 5                                                         ______________________________________                                         ##STR550##                  (IX)                                             Examples of the hydrazine derivatives of the                                  formula (IX)                                                                  Ex.                                                                           No.    R.sup.1       R.sup.2      m.p. (°C.)                           ______________________________________                                        IX-2   OCH.sub.3     C.sub.2 H.sub.5                                                                            120                                         IX-3   OCH.sub.3     C.sub.3 H.sub.7                                                                            125                                         IX-4   OCH.sub.3     CH(CH.sub.3).sub.2                                                                         127                                         IX-5   OCH.sub.2 C.sub.6 H.sub.5                                                                   CH.sub.3     100                                         IX-6                                                                                  ##STR551##   C.sub.2 H.sub.5                                                                            174                                         IX-7                                                                                  ##STR552##   C.sub.3 H.sub.7                                                                            180                                         IX-8   OC.sub.2 H.sub.5                                                                            C.sub.3 H.sub.7                                                                            119                                         IX-9                                                                                  ##STR553##   CH(CH.sub.3).sub.2                                                                         150                                         IX-10  OCH.sub.3     C.sub.4 H.sub.9                                                                            134                                         IX-11                                                                                 ##STR554##   C.sub.4 H.sub.9                                                                            159                                         IX-12                                                                                 ##STR555##                                                                                  ##STR556##  188                                         IX-13  OCH.sub.3                                                                                    ##STR557##  140                                         IX-14  CH.sub.2CHCH.sub.2                                                                          C.sub.3 H.sub.7                                                                            134                                         IX-15                                                                                 ##STR558##   CH.sub.2 OC.sub.2 H.sub.5                                                                   97                                         ______________________________________                                    

STARTING SUBSTANCES OF THE FORMULA (IV): EXAMPLE (IV-1) ##STR559##

6.4 g (0.05 mol) of 5-ethyl-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-oneare dissolved in 80 ml of tetrahydrofuran, and 1.8 g (0.06 mol) ofsodium hydride (80% of substance) are added under nitrogen. After themixture has been stirred for one hour at 20° C., 7.9 g (0.05 mol) ofphenyl chloroformate are added dropwise, and the reaction mixture isstirred at 20° C. for a further 20 hours. After the mixture has beenconcentrated, the residue is taken up in methylene chloride, and themixture is washed with water, dried with sodium sulphate and filtered.The liltrate is concentrated, the residue is triturated with diethylether, and the product which has been obtained in crystalline form isisolated by filtration with suction.

This gives 4.5 g (36% of theory) of5-ethyl-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one ofmelting point 141° C.

For example the compounds of the formula (IV) listed in Table 6 belowcan also be prepared analogously to Example (IV-1).

                  TABLE 6                                                         ______________________________________                                         ##STR560##                   (IV)                                            Examples of the compounds of the formula (IV)                                 Ex.                                                                           No.   R.sup.1      R.sup.2      Z    m.p. (°C.)                        ______________________________________                                        IV-2  C.sub.3 H.sub.7                                                                            C.sub.3 H.sub.7                                                                            C.sub.6 H.sub.5                                                                    88                                       IV-3  OCH.sub.3    C.sub.3 H.sub.7                                                                            C.sub.6 H.sub.5                                                                    82                                       IV-4  CH.sub.3     C.sub.3 H.sub.7                                                                            C.sub.6 H.sub.5                                                                    84                                       IV-5  NH.sub.2     C.sub.3 H.sub.7                                                                            C.sub.6 H.sub.5                                                                    133                                      IV-6  NH.sub.2     CH.sub.3     C.sub.6 H.sub.5                                                                    82                                       IV-7                                                                                 ##STR561##  C.sub.2 H.sub.5                                                                            C.sub.6 H.sub.5                                                                    152                                      IV-8  OC.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                                                            C.sub.6 H.sub.5                               IV-9  OCH.sub.2 CHCH.sub.2                                                                       CH.sub.3     C.sub.6 H.sub.5                               IV-10                                                                                ##STR562##  C.sub.4 H.sub.9                                                                            C.sub.6 H.sub.5                               IV-11 CH.sub.3                                                                                    ##STR563##  C.sub.6 H.sub.5                               IV-12 NHCH.sub.3   C.sub.2 H.sub.5                                                                            C.sub.6 H.sub.5                               IV-13 CH.sub.3     CH.sub.2 C.sub.6 H.sub.5                                                                   C.sub.6 H.sub.5                               IV-14 CH.sub.3     NHCH(CH.sub.3).sub.2                                                                       C.sub.6 H.sub.5                               IV-15 N(CH.sub.3).sub.2                                                                          N(CH.sub.3).sub.2                                                                          C.sub.6 H.sub.5                               IV-16                                                                                ##STR564##                                                                                 ##STR565##  C.sub.6 H.sub.5                               IV-17 OC.sub.2 H.sub.5                                                                            ##STR566##  C.sub.6 H.sub.5                               IV-18 OC.sub.3 H.sub.7                                                                           C.sub.2 H.sub.5                                                                            C.sub.6 H.sub.5                               IV-19 C.sub.2 H.sub.5                                                                            C.sub.4 H.sub.9                                                                            C.sub.6 H.sub.5                               IV-20 CH(CH.sub.3).sub.2                                                                         CH(CH.sub.3).sub.2                                                                         C.sub.6 H.sub.5                               IV-21 OCH.sub.3    C.sub.2 H.sub.5                                                                            C.sub.6 H.sub.5                                                                    89                                       IV-22                                                                                ##STR567##  C.sub.3 H.sub.7 -n                                                                         C.sub.6 H.sub.5                                                                    104                                      ______________________________________                                    

USE EXAMPLES

In the following use examples, the known herbicide isocarbamide, offormula (A) below, is used as comparison substance:

The formulae of the compounds according to the invention used in the UseExamples are listed individually below in conjunction with the number ofthe Preparation Examples: ##STR569##

EXAMPLE A

Pre-emergence test

Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight ofalkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added, and the concentrate is dilutedwith water to the desired concentration.

Seeds of the test plants are sown in normal soil and, after 24 hours,watered with the preparation of active compound. It is expedient here tokeep constant the amount of water per unit area. The concentration ofactive compound in the preparation is of no importance, only the amountof active compound applied per unit area being decisive. After threeweeks, the degree of damage of the plants is rated in % damage incomparison with the development of the untreated control. The figuresdenote:

0% =no action (like untreated control)

100% =total destruction

In this test a clearly superior activity compared with the prior art isshown, for example, by the compounds of Preparation Examples 2, 6, 8,12, 13, 16, 17, 18, 19, 20, 26, 27, 28, 29, 34, 37, 39, 40 and 133.

EXAMPLE B

Post-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added, and the concentrate is dilutedwith water to the desired concentration.

Test plants having a height of 5-.cm are sprayed with the preparation ofactive compound in such a way that the specifically desired amounts ofactive compound per unit area are applied. The concentration of thespray liquor is chosen in such a way that the specifically desiredamounts of active substance are applied in 1000 l of water/ha. Afterthree weeks, the degree of damage of the plants is rated in % damage incomparison with the development of the untreated control. The figuresdenote:

0%=no action (like untreated control)

100%=total destruction

In this test a clearly superior activity compared with the prior art isshown, for example, by the compounds of Preparation Examples 2, 4, 5, 6,7, 8, 12, 13, 14, 15, 16, 17, 18, 19, 20, 26, 27, 28, 29, 30, 32, 33,34, 35, 37, 39, 40, 126, 128 and 133.

EXAMPLE C

Pyricularia test (rice) / protective

Solvent: 12,5 parts by weight of acetone

emulsifier: 0,3 parts by weight of alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, and-theconcentrate is diluted with water and the stated amount of emulsifier tothe desired concentration. To test for protective activity, young riceplants are sprayed with the preparation of active compound untildripping wet. After the spray coating has dried off, the plants areinoculated with an aqueous spore suspension of Pyricularia orycae. Theplants are then placed in a greenhouse at 100% relative atmospherichumidity and 25° C.

Evaluation of the disease infestation is carried out 4 days after theinoculation.

In this test, a very good activity is shown, for example, by thecompounds according to the following preparation examples:9, 12, 13, 20,30, 31, 32, 33, 34, 35, 36, 37, 140, 145, 147, 152, 153, 154.

EXAMPLE D

Pyricularia Test (rice) / systemic

Solvent : 12,5 parts by weight of acetone Emulsifier: 0,3 parts byweight of alkylaryl-polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, and theconcentrate is diluted with water and the stated amount of emulsifier,to the desired concentration.

To test for systemic properties, standard soil in which young plantshave been grown is watered with 40 ml of the preparation of activecompound. 7 days after the treatment, the plants are inoculated with anaqueous spore suspension of Pyricularia oryzae. Thereafter, the plantsremain in a greenhouse at a temperature of 25° and a relativeatmospheric humidity of 100% until they are evaluated. Evaluation of thedisease infestation is carried out 4 days after the inoculation.

In this test, an excellent activity is shown, for example, by thecompounds according to the following preparation examples: 9, 12, 13,20, 30, 31, 32, 33, 34, 35, 36, 37, 140, 145,147,152, 153, 154.

It will be appreciated that the instant specification and claims are setforth by way of illustration and not limitation, and that variousmodifications and changes may be made without departing from the spiritand scope of the present invention.

We claim:
 1. A triazolinone of the formula (IIa) ##STR570## wherein##STR571##
 2. The triazolinone of claim 11, wherein R¹ is ##STR572## andR² is C₃ H₇.
 3. The triazolinone of claim 1, wherein R¹ is ##STR573##and R² is CH(CH₃)₂.
 4. The triazolinone of claim 1, wherein R¹ is##STR574## and R² is C₄ H₉.
 5. The triazolinone of claim 1, wherein R¹is CH₃ and R² is ##STR575##
 6. The triazolinone of claim 1, wherein R¹is C₂ H₅ and R² is ##STR576##
 7. The triazolinone of claim 1, wherein R¹is C₃ H₇ and R² is ##STR577##
 8. The triazolinone of claim 1, wherein R¹is ##STR578##
 9. The triazolinone of claim 1, wherein R¹ is ##STR579##and R² is H.
 10. The triazolinone of claim 1, wherein R¹ is ##STR580##and R² is C₂ H₅.
 11. The triazolinone of claim 1, wherein R¹ is --CH₂CH═CH₂ and R² is CH₃ .
 12. The triazolinone of claim 1, wherein R¹ is##STR581## and R² is CH₃.
 13. The triazolinone of claim 1, wherein R¹ isCH₃ and R² is --CH₂ OCH₃.
 14. The triazolinone of claim 1, wherein R¹ is##STR582## and R² is --CH₂ OCH₃.
 15. The triazolinone of claim 1,wherein R¹ is ##STR583## and R² is --CH₂ OC₂ H₅.
 16. The triazolinone ofclaim 1, wherein R¹ is ##STR584## and R² is --N(CH₃)₂.